118129-60-5Relevant articles and documents
Tubular Perylene Bisimide Macrocycles for the Recognition of Geometrical Isomers of Azobenzenes
Bhargava, Samarth,Türel, Tankut,Valiyaveettil, Suresh
, p. 3092 - 3100 (2020)
Perylene bisimide-based materials are good candidates for photosensitive applications. Herein, we report synthesis, characterization, and complexation studies of perylene bisimide macrocycles obtained through bayside coupling. The isomeric macrocycles incorporated with interesting optical properties and tubular-shaped cavities are able to recognize geometric isomers of azobenzenes and aromatic amines. Such selective recognition is useful toward developing potential sensors for interesting isomeric pairs in the future.
Synthesis and characterization of perylene diimide based molecular multilayers using CuAAC: Towards panchromatic assemblies
Beauvilliers, Evan E.,Topka, Michael R.,Dinolfo, Peter H.
, p. 32866 - 32875 (2014)
Three perylene diimides (PDI) were synthesized with propargyl groups at the diimide positions to enable the fabrication of molecular multilayer thin films via sequential copper(i) catalyzed azide-alkyne cycloaddition (CuAAC) coupling reactions in a layer-by-layer (LbL) fashion. The new PDIs with phenoxy (PhO-PDI), dodecylthiol (Thiol-PDI), and pyrrolidine (Pyrr-PDI) substituents in bay positions have optical absorption spectra that span a large portion of the visible region. Multilayer growth on 11-azidoundecylsiloxane coated silica glass and indium tin oxide (ITO) surfaces was demonstrated up to 10 bilayers of each PDI with 1,3,5-tris(azidomethyl)-benzene (N3Mest) via optical and infrared spectroscopy. Polarized UV-visible absorption measurements showed a strong dependence on the orientation of the film in the light path and was consistent with a preferential orientation of the PDI molecules in the film at 40-42° with respect to the substrate surface. Grazing-angle attenuated total reflectance (GATR) infrared spectra of the films show an increase in content of unreacted azides during multilayer growth from N3Mest as a result of the smaller molecular footprint as compared to the PDI components. Electrochemical scans of the multilayer films grown on ITO exhibited reversible two-electron reduction waves for the PDIs with linear increases in charge with bilayer growth. The electrochemically derived surface coverages of PDIs averaged 1.2-1.3 × 1014 molecules per cm2 for each layer added to the multilayer films. The flexibility of the CuAAC based LbL assembly methodology is highlighted by the assembly of a mixed multilayer film containing five layers of each PDI, resulting in a panchromatic film that is a summation of individual chromophores. This journal is the Partner Organisations 2014.
Highly uniform supramolecular nano-films derived from carbazole-containing perylene diimide: Via surface-supported self-assembly and their electrically bistable memory behavior
Khan, Qudrat Ullah,Tian, Guofeng,Bao, Lin,Qi, Shengli,Wu, Dezhen
, p. 11506 - 11515 (2018)
For electrical memory applications, two perylenetetracarboxylic diimide (PDI) derivatives, N,N′-(6-carbazole hexyl)-1,7-di(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxylic diimide (PDI-6Cz) and N,N′-(2-carbazole ethyl)-1,7-di(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxylic diimide (PDI-2Cz), were synthesized and their surface-supported self-assembly behaviors were investigated. PDI-2Cz tends to self-organize into regular rods, which are proved to be hexagonal lattices with single crystal nature, based on which memory device fabrication and electrically bistable behavior evaluation are technically infeasible. Whereas PDI-6Cz readily self-assembles into highly uniform nano-films with a considerably smooth surface, in which the X-ray diffraction study indicates strong π-π stacking between the aromatic skeletons. Further characterization indicates that sandwich memory devices using a PDI-6Cz nano-film as the active layer exhibit reprogrammable flash-type memory behavior with a switching-on voltage of ca. 0.8 V and an ON/OFF current ratio of 104. Besides, the devices exhibit excellent long-term operation stability, enduring up to 108 reading cycles without obvious current variation and an ultrafast switching response period of less than 20 ns. Photophysical and electrochemical measurements and DFT molecular simulations were conducted to determine the electronic transition occurring in the supramolecular self-assembled nano-film. Compared with organic storage materials based on polymers, the current memory device exhibits lower threshold voltage and more rapid response speed, which provides a new way for developing high-performance organic data storage materials.
Specific interactions with intra- and intermolecular G-quadruplex DNA structures by hydrosoluble coronene derivatives: A new class of telomerase inhibitors
Franceschin, Marco,Alvino, Antonello,Casagrande, Valentina,Mauriello, Clementina,Pascucci, Emanuela,Savino, Maria,Ortaggi, Giancarlo,Bianco, Armandodoriano
, p. 1848 - 1858 (2007)
In developing G-quadruplex interactive telomerase inhibitors two main features have to be taken into account: the hydrophobic interactions with the G-quartet plane and the electrostatic interactions with the negatively charged phosphates of the four grooves. In this paper, we report the synthesis of four hydrosoluble coronene derivatives, which are characterized by a large hydrophobic aromatic core and four orthogonal hydrophilic side chains. We have studied their ability to induce both inter- and intramolecular G-quadruplex structures and found a significant selectivity of all the coronene derivatives for the intramolecular G-quadruplex. The efficiency in inhibiting human telomerase has been evaluated in a cell-free system and the experimental results correlate with the relative affinities of these compounds for the G-quadruplex monomeric structure, as derived by molecular modelling simulations. Thus, the coronene derivatives can be considered as a new class of telomerase inhibitors, although further investigations are surely necessary to fully exploit their features.
Controllable Monobromination of Perylene Ring System: Synthesis of Bay-Functionalized Perylene Dyes
Takahashi, Masaki,Asaba, Kyohei,Lua, Trinh Thi,Inuzuka, Toshiyasu,Uemura, Naohiro,Sakamoto, Masami,Sengoku, Tetsuya,Yoda, Hidemi
, p. 624 - 631 (2018)
Practical synthesis of bay-monofunctionalized perylene dyes has been developed based on controllable NBS bromination of tetrabenzyl perylene-3,4,9,10-tetracarboxylate. The ability to perform the convenient and high-yielding synthesis highlights the potential utility of our multifunctional approach to access a diverse range of new perylene systems.
Synthesis of regioisomerically pure 1,7-dibromoperylene-3,4,9,10- tetracarboxylic acid derivatives
Sengupta, Sanchita,Dubey, Rajeev K.,Hoek, Rob W. M.,Van Eeden, Sjoerd P. P.,Gunbas?, D. Deniz,Grozema, Ferdinand C.,Sudh?lter, Ernst J. R.,Jager, Wolter F.
, p. 6655 - 6662 (2014)
The perylene derivative 1,7-dibromoperylene-3,4,9,10-tetracarboxylic tetrabutylester has been obtained in regioisomerically pure form, by employing a highly efficient, scalable, and robust synthesis starting from commercially available perylene-3,4,9,10-tetracarboxylic bisanhydride. Subsequently, this compound is utilized for the synthesis of extremely valuable and versatile regioisomerically pure intermediates, namely, 1,7-dibromoperylene-3,4,9,10- tetracarboxylic dibutylester monoanhydride, 1,7-dibromoperylene-3,4,9,10- tetracarboxylic bisanhydride, and 1,7-dibromoperylene monoimid monoanhydride. These compounds possess at least one anhydride functionality in addition to the 1,7 bromo substituents and thus allow for a virtually limitless attachment of substituents both at the "peri" and the "bay" positions. The intermediate 1,7-dibromoperylene monoimide monoanhydride is of special interest as it provides access to unsymmetrically imide-substituted 1,7-dibromoperylene derivatives, which are not accessible by previously known procedures. Finally, substitution of the 1,7 bromine atoms in the bay area by phenoxy groups, which is a generally applied reaction for 1,7-dibromoperylene bisimides, was proven to be equally effective for a 1,7-dibromoperylene tetraester and a 1,7-dibromoperylene diester monoimid.
Synthesis and photoelectric properties of donor-acceptor-donor molecule containing perylene diimide
Jiao, Chun Ming,Li, Bing Jun,Yi, Si Li,Xu, Qing
, p. 8049 - 8052 (2014)
In this paper, a novel perylene diimide derivative 1,7-bis[N,N-bis(4-phenyl)aniline]perylene diimide (PDI-TPA) was synthesized and characterized by IR spectroscopy, 1H NMR and elemental analysis. Besides, solubility and photoelectric properties of 1,7-bis[N,N-bis(4- phenyl)aniline]perylene diimide were studied. Results show that 1,7-bis[N,N-bis(4-phenyl)aniline]perylene diimide exhibits excellent solubility in common solvents. The absorption bands span a wide range of the visible spectra and optical band gap is 1.68 eV. In addition, 1,7-bis[N,N-bis(4-phenyl)aniline]perylene diimide exhibits an ambipolar behaviour, the highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level are -5.64 eV and -3.94 eV, respectively.
Two novel rhodamine-perylenediimide fluorescent probes: Synthesis, photophysical properties, and cell imaging
Cheng, Huan-Ren,Qian, Ying
, p. 879 - 886 (2016)
In this study, two novel dual-switch fluorescent chemosensors based on rhodamine-peryleneiimide have been designed and synthesized. The dual-switching behaviors of the sensors were based on the structural transformations of rhodamine and an intramolecular photoinduced electron transfer (PET) process from rhodamine to perylenediimide. These probes exhibited excellent sensitivity to protons with enhanced fluorescence emission from 500 nm to 580 nm. The fluorescence changes of probes were reversible within a wide range of pH values from 2.0 to 11.0. Moreover, the sensors exhibited high selectivity, short response time, and long lifetime toward protons. The possible mechanism was investigated by the DFT calculation and 1H NMR. According to the experiment of confocal laser scanning microscopy, these probes could be used to detect the acidic pH variations in living cells.
1,6-Disubstituted perylene bisimides: Concise synthesis and characterization as near-infrared fluorescent dyes
Fan, Liqiang,Xu, Yanping,Tian, He
, p. 4443 - 4447 (2005)
Detailed studies on bromination and subsequent imidization of perylene bisanhydride were reported. 1,6,7,12-Tetrabromoperylene bisimide was obtained in an optimized high yield. In addition, 1,6-disubstituted regioisomer was separated for the first time in isomerically pure form, and the structure was confirmed by 1H NMR, MS, element analysis, and photophysical measurements. By using a mixture of regioisomers 1,6- and 1,7-dibromo-perylene bisimide, 1,6-dipiperidinylperylene bisimides (1,6-Piper-Pery) were synthesized, purified, and their fluorescence were measured with a peak at 760 nm. These compounds can be used as stable near-infrared absorbing and fluorescent dyes.
Synthesis of regioisomerically pure piperidine substituted perylenebisimide NIR dyes: A comparative study of spectroscopic, electrochemical and crystalline properties
Hussain, Ejaz,Zhou, Huipeng,Yang, Na,Shahzad, Sohail Anjum,Yu, Cong
, p. 211 - 224 (2017)
New regioisomerically pure green and blue dyes i.e. 1,7 and 1,6 piperidine substituted perylenebisimides (1A, 1B, 2A, 2B) were synthesized. Photophysical properties were compared with unsubstituted and brominated perylenebisimide analogues (1, 1PBr2, 2, 2PBr2). Piperidine was substituted on the bay region after imidization of dibromoperylene-3,4,9,10-tetracaboxylic dianhydride which induces strong bathochromic shifts. Large bathochromic shifts lower the optical band gaps which is the key feature of NIR absorbing fluorescent dyes with improved photovoltaic efficiencies. All synthesized fluorophores were characterized by NMR and Mass spectrometry. Photophysical properties were evaluated by UV–Vis, fluorimetry, and cyclic voltammetry. Fluorescence quantum yields were estimated by adopting a gradient method. The well-defined sharp peaks in X-ray diffraction pattern confirmed the crystalline nature of 1A and 1B. In contrast 2A and 2B were found non-crystalline. Thermal analysis by TG-DSC further explored the stability and phase transitions in dyes. HOMO and LUMO molecular orbitals were depicted by using density functional theory (DFT) at B3LYP/6–31(d,p). Electrochemical behaviors probed by cyclic voltammogram revealed dominant reversible oxidation reactions for 1,7 regioisomers (1A, and 2A) while both reversible oxidations and reductions were observed in 1,6 isomers (1B and 2B). Other structural analogues 1, 1PBr2, 2, 2PBr2 displayed reversible reductions. Thus a regular trend of changes in optical and electrical properties was observed on bromine and piperidine substitution. The observed outstanding properties clearly justify that our compounds might be promising candidates for various future applications such as biosensors, biomarkers, semiconductors, charge transporters, and stable fluorescent dyes.
New hydrosoluble perylene and coronene derivatives
Franceschin, Marco,Alvino, Antonello,Ortaggi, Giancarlo,Bianco, Armandodoriano
, p. 9015 - 9020 (2004)
Several lipophilic perylene and coronene derivatives, employed mainly as liquid crystalline dyes are known and their synthesis has been widely studied. We have applied an analogue strategy using hydrophilic substituents to obtain highly water soluble perylene diimides (4) and a new hydrosoluble coronene derivative (CORON, 6), whose molecular features appear particularly suitable for inducing G-quadruplex DNA structures and inhibiting human telomerase.
1,6- and 1,7-regioisomers of dicyano-substituted perylene bisimides: Synthesis, optical and electrochemical properties
Tsai, Hsing-Yang,Chang, Che-Wei,Lin, Chi-Wei,Chen, Kew-Yu
, p. 280 - 286 (2015)
In this study, 1,6- ad 1,7-regioisomers of dicyano-substituted perylene bisimides (1,6-C and 1,7-C) were synthesized and successfully isolated from their regioisomeric mixture using conventional methods of separation, and subsequently characterized by 400
Water-soluble and highly emissive near-infrared nano-probes by co-assembly of ionic amphiphiles: Towards application in cell imaging
Xing, Yuzhi,Li, Dahua,Dong, Bin,Wang, Xiaocheng,Wu, Chengfeng,Ding, Lan,Zhou, Shixin,Fan, Jian,Song, Bo
, p. 8059 - 8066 (2019)
Water-soluble near-infrared (NIR) fluorescent dyes are extremely valuable in cell imaging. We here designed and synthesized an amphiphilic fluorescent dye (denoted by PBI-TPE-11), a bolaamphiphile bearing conjugated tetraphenylethylene and perylene bisimide in the middle and two aliphatic pyridinium groups at both ends. PBI-TPE-11 self-assembled into flake-like nanostructures in aqueous solution and showed very weak fluorescence emission from 600 to 830 nm, covering the NIR region. This result seems discrepant with that previously reported in the literature, where the conjugation of PBI and TPE was proven enhance aggregation induced emission. Very interestingly, both the morphology and the emission intensity were altered by the addition of sodium dodecyl benzene sulfonate (SDBS). Co-assembly of PBI-TPE-11 and SDBS formed nanowires, observed by using an atomic force microscope. Moreover, the emission of the co-assemblies was much stronger than that of the assemblies of neat PBI-TPE-11. An exciting quantum yield (QY) of 15% was obtained for the co-assemblies, while pure PBI-TPE-11 showed a QY of merely 0.2%. Finally, the co-assemblies were successfully applied in labeling HeLa cells, and high viability and high contrast fluorescence images were achieved.
1,7,9,10-Tetrasubstituted PMIs Accessible through Decarboxylative Bromination: Synthesis, Characterization, Photophysical Studies, and Hydrogen Evolution Catalysis
Costabel, Daniel,Skabeev, Artem,Nabiyan, Afshin,Luo, Yusen,Max, Johannes B.,Rajagopal, Ashwene,Kowalczyk, Daniel,Dietzek, Benjamin,W?chtler, Maria,G?rls, Helmar,Ziegenbalg, Dirk,Zagranyarski, Yulian,Streb, Carsten,Schacher, Felix H.,Peneva, Kalina
, p. 4081 - 4088 (2021)
In this work, we present a new synthetic strategy for fourfold-substituted perylene monoimides via tetrabrominated perylene monoanhydrides. X-ray diffraction analysis unveiled the intramolecular stacking orientation between the substituents and semicircular packing behavior. We observed the remarkable influence of the substituent on the longevity and nature of the excited state upon visible light excitation. In the presence of poly(dehydroalanine)-graft-poly(ethylene glycol) graft copolymers as solubilizing template, the chromophores are capable of sensitizing [Mo3S13]2? clusters in aqueous solution for stable visible light driven hydrogen evolution over three days.
Regioisomers of perylenediimide: Synthesis, photophysical, and electrochemical properties
Keerthi, Ashok,Valiyaveettil, Suresh
, p. 4603 - 4614 (2012)
A series of conjugation extended donor-acceptor 1,6- and 1,7-regiomers of perylenediimide were synthesized, separated, and characterized. The photophysical, electrochemical, and thermal properties of these compounds were investigated and compared. The absorption spectra of 1,6-substituted PDI showed blue shift as compared to its 1,7-substituted PDI. At the same time, the emission spectrum showed no significant differences among the regiomers. Both 1,6- and 1,7-regiomers were thermally stable up to 450 ?°C and showed different melting and crystallization transitions. The electrochemical studies did not show significant differences in oxidation and redox potentials owing to similar HOMO/LUMO gap of 1,6- and 1,7-regiomers, which is also supported by theoretical calculations. Comparison of properties of a series of 1,6- or 1,7-substituted PDIs showed significant differences. Such regiomerically pure compounds can offer certain advantages in applications, which are currently being investigated. ? 2012 American Chemical Society.
Spin-carrying naphthalenediimide and perylenediimide derivatives
Nakatsuji, Shin'ichi,Aoki, Kazunori,Akutsu, Hiroki,Yamada, Jun-Ichi,Kojima, Takahiro,Nishida, Jun-Ichi,Yamashita, Yoshiro
, p. 1079 - 1085 (2010)
A couple of naphthalenediimide 4 and 5 and series of perylenediimide derivatives 6-9 carrying TEMPO radical were prepared and their redox, FET, and magnetic properties were investigated. The radical compounds 4 and 6-9 were found to show antiferromagnetic interactions obeying the Curie-Weiss model, while the naphthalenediimide derivative 5 exhibited a singlet-triplet magnetic behavior and it could be well understood by the short oxygen-to-oxygen distance between the spin centers observed in its crystal structure. Owing presumably to their appropriate reduction potentials and structural motifs, exhibitions of n-type FET properties were disclosed in these radical compounds with mobilities of the order from 10-5 to 10-8cm2 V-1 s-1 and apparent increase of mobilities was observed in the radical compounds 5 and 7 by the surface treatment with HMDS.
Low band gap thiophene-perylene diimide systems with tunable charge transport properties
Balaji, Ganapathy,Kale, Tejaswini S.,Keerthi, Ashok,Della Pelle, Andrea M.,Thayumanavan,Valiyaveettil, Suresh
, p. 18 - 21 (2011)
Perylenediimide-pentathiophene systems with varied architecture of thiophene units were synthesized. The photophysical, electrochemical, and charge transport behavior of the synthesized compounds were studied. Both molecules showed a low band gap of ～1.4 eV. Surprisingly, the molecule with pentathiophene attached via β-position to the PDI unit upon annealing showed a predominant hole mobility of 1 × 10-4 cm2 V-1 s-1 whereas the compound with branched pentathiophene attached via β-position showed an electron mobility of 9.8 × 10 -7 cm2 V-1 s-1. This suggests that charge transport properties can be tuned by simply varying the architecture of pentathiophene units.
Coronene-Containing N-Heteroarenes: 13 Rings in a Row
Endres, Alexander H.,Schaffroth, Manuel,Paulus, Fabian,Reiss, Hilmar,Wadepohl, Hubert,Rominger, Frank,Kr?mer, Roland,Bunz, Uwe H. F.
, p. 1792 - 1795 (2016)
We describe the modular synthesis of three novel large N-heteroarenes, containing 9, 11, and 13 annulated rings. This modular system features fused azaacene units to a coronene nucleus. We evaluate the optical and electronic properties and the solid-state packing of the targets. The electronic properties of the 13-ring N-heteroarene allow the fabrication of a proof-of-concept thin-film transistor. Electron mobilities up to 8 × 10-4 cm/(V s) were obtained for polycrystalline films.
Synthesis, mesomorphic and photophysical properties of novel triads and pentads of perylene liquid crystals with cholesterol units at the bay-position
Zhu, Mingguang,Guo, Hongyu,Yang, Fafu,Wang, Zusheng
, p. 4320 - 4328 (2017)
Series of triads and pentads of perylene derivatives with two cholesterol units at the bay-position or four cholesterol units on both bay-position and imide position were designed and synthesized in yields of 55-65%. The influence of the different number and position of cholesterol substituents on mesomorphic properties and photophysical properties was studied. The results suggested that, in comparison with similar perylene derivatives with alkyl units at the imide position, the perylene liquid crystals with alkyl units at the bay-positions not only maintained excellent mesomorphic properties but also enhanced the fluorescence greatly. More cholesterol units resulted in a lower mesophase temperature, wider phase transfer temperature range, and higher fluorescence. A long spacer between perylene and cholesterol units led to more excellent mesomorphic properties and higher fluorescence.
Regioisomerically pure 1,7-dibromo-substituted perylene bisimide dyes: Efficient synthesis, separation, and characterization
Ma, Jiajun,Yin, Leicheng,Zou, Gang,Zhang, Qijin
, p. 3296 - 3302 (2015)
1,7-Dibromo-substituted perylene bisimides have been obtained in yields of at least 60% in regioisomerically pure form by treating the commonly used dibromoperylene-3,4,9,10-tetracarboxylic dianhydride with 2-(diethylamino)ethylamine or 2-(dimethylamino)ethylamine and then separating the 1,7-isomer from the regioisomeric mixtures by conventional column chromatography and without recrystallization. The individual regioisomers were fully characterized by 1H NMR spectroscopy and HRMS. The signals of the protons located in the aromatic region and neighboring the imide nitrogen atom were utilized to confirm the chemical structures of the isomers. The 1,7-dibromo isomer obtained with 2-(dimethylamino)ethylamine in such a convenient and efficient way was further used to prepare 1,7-disubstituted perylene bisimide derivatives by saponification, amidation, and then bay-position substitution reactions. These compounds exhibited a significant redshift and broadening of their absorption and emission in optical spectroscopy analysis.
Asymmetric perylene bisimide dyes with strong solvatofluorism
Luo, Ming-Hui,Chen, Kew-Yu
, p. 456 - 464 (2013)
Two asymmetric perylene bisimide dyes, 1-cyano-7-piperidinylperylene bisimide (1) and 1-bromo-7-piperidinylperylene bisimide (2), were synthesized and fully characterized. These molecules undergo an excited-state intramolecular electron transfer reaction, resulting in a unique charge transfer emission, of which the peak wavelength exhibits strong solvatochromism. They show both larger ground-state and excited-state dipole moments than those of the symmetric perylene bisimide 3; the dipole moments of these compounds have been estimated using density functional theory calculations and the Lippert-Mataga equation. Furthermore, these dyes (1-3) display good thermal stability as well as good optical stability and reversible redox properties. Their spectroscopic properties in various conditions and complementary time-dependent density functional theory calculations are reported.
Pyrene fused perylene diimides: Synthesis, characterization and applications in organic field-effect transistors and optical limiting with high performance
Zhan, Xuejun,Zhang, Ji,Tang, Sheng,Lin, Yuxuan,Zhao, Min,Yang, Jie,Zhang, Hao-Li,Peng, Qian,Yu, Gui,Li, Zhen
, p. 7156 - 7159 (2015)
Three pyrene fused PDI derivatives have been obtained, in which totally different properties were observed when adopting different fusing types. For bilaterally benzannulated PDIs, through spin-coating, bottom-contact OFET devices exhibited a p-type mobility up to 1.13 cm2 V-1 s-1, with an on/off ratio of 108 in air. This journal is
Bay region borylation of perylene bisimides
Dey, Somnath,Efimov, Alexander,Lemmetyinen, Helge
, p. 5955 - 5958 (2011)
Novel bispinacolborane-N,N′-bis(octyl)-3,4,9,10- perylenetetracarboxylic acid bisimide (PBI) was synthesized in high yield. The title compound is a key intermediate in the preparation of PBI aryl derivatives through Suzuki cross-coupling by using a large variety of easily accessible aryl halides. The benign effect of a nonpolar solvent, mild base, and high reaction temperature on the borylation reaction was studied, and the reaction conditions were optimized accordingly. To demonstrate the potential and flexibility of the proposed building block, two corresponding bisarylperylene bisimides were prepared in high yields. For the first time, an efficient and straightforward method was developed for thesynthesis of bis-pinacolborane-N,N′-bis(octyl) -3,4,9,10-perylene tetracarboxylic bisimide derivatives by using a commercially available Pd catalyst. Two Suzuki cross-coupling reactions of novel bispinacolborane perylene derivative are also reported.
Stimuli-responsive circularly polarized luminescence from an achiral perylenyl dyad
Li, Junfeng,Yang, Chenglong,Peng, Xuelei,Qi, Qi,Li, Yonghua,Lai, Wen-Yong,Huang, Wei
, p. 8463 - 8470 (2017)
Stimuli-responsive circularly polarized luminescence (CPL) was successfully achieved through fine-tuning the conformation of a perylenyl dyad by using external stimuli. Monomer CPL was clearly detected from an inherent achiral monochromophore system in a simple perylene-carbazole dyad, and concentration-dependent CPL was observed from 'good solvent', giving an excimer-like CPL emission with a peak maximum at 643 nm. Moreover, the CPL bands depended on the aggregated state, which was identical to the emission changes in the THF-H2O system. It is noteworthy that the perylene-carbazole dyad emitted efficient CPL in thin films even without annealing processes. The specific perylenyl-carbazole structure plays a crucial role in CPL in response to the external environment. This novel molecular design strategy opens up a new perspective for the future development of smart CPL-active organic dyads.
Donor-acceptor copolymers with 1,7-regioisomers of: N, N ′-dialkylperylene-3,4,9,10-tetracarboxydiimide as materials for photonics
Cimrová, Věra,Vyprachticky, Drahomír,Pokorná, Veronika,Babi?ová, Petra
, p. 14678 - 14692 (2019)
Donor-acceptor (D-A) copolymers containing N,N′-dialkylperylene-3,4,9,10-tetracarboxydiimide electron-acceptor units with dodecyl (DDPDI) or 2-ethylhexyl (EHPDI) substituents and three different electron-donor units (9,9-dioctylfluorene, 9-(2-ethylhexyl)carbazole or 9-(heptadecan-9-yl)carbazole) were synthesized by Suzuki coupling and were then characterized. Their thermal, photophysical, electrochemical and spectroelectrochemical properties were studied. The effects of the alkyl side chain combination on the properties were evaluated and are discussed. Despite large differences in the absorption spectra of the individual DDPDI and EHPDI units or monomers in solutions and thin films, the absorption spectra of the copolymers in solutions and thin films exhibited similar shapes. More pronounced side chain effects were observed in the photoluminescent (PL) behaviour than in the absorption behaviour. Different alkyl side chains on the D-A copolymers similarly affected the visible absorption band contributions in the solutions and thin films, but the exhibited effects were different for the PL spectra and efficiency. The copolymers exhibited reversible reduction and irreversible oxidation. The ionization potential and bandgap values were influenced by the donor unit and by the perylene-3,4,9,10-tetracarboxydiimide (PDI) side chain nature. Spectroelectrochemical changes are reported, and potential sensing applications are outlined.
Preparation method and application of nucleon targeted photo-thermal reagent based on perylene bisimide
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Paragraph 0031-0033, (2021/09/08)
The invention discloses a preparation method and application of a perylene bisimide-based nucleolus targeting photo-thermal reagent. To the method, bromine substituted perylene imide is firstly obtained through reaction of liquid bromine and perylene anhydride. The substitution group is then introduced into the imide position and the bay position by the reaction of the amino group and the acid anhydride and nucleophilic substitution reaction of the amino group and the bromine, namely, the perylene bisimide-based nucleolus targeting photo-thermal agent is obtained. The synthetic photothermal reagent is a compound capable of specifically and strongly binding with a nucleic acid, and the binding force enables the photothermal reagent to be rapidly taken (within three minutes) and enriched to DNA by cells. RNA, The targeted effect on nucleolus kernels is superior to that of commercialized dye nuclei green. The synthetic photothermal reagent is good in water solubility, good in light, heat and chemical stability, high in light absorption in the near infrared region, good in photothermal conversion efficiency, excellent in photo-thermal killing effect on tumor cells and capable of realizing photothermal therapy of cancer cells.
Perylene diimide derivative-based near-infrared two-region aggregation-induced light-emitting molecule and preparation method and application thereof
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Paragraph 0048-0055, (2021/09/29)
The invention provides a perylene diimide derivative-based near-infrared two-region aggregation-induced light-emitting molecule and a preparation method and application thereof. Firstly, perylene diimide is used as a receptor structural unit to perform coupling reaction with a large-sized donor unit to obtain a near-infrared two-region aggregation-induced light-emitting molecule based on a perylene diimide structure. The molecule is connected with a donor structure with a larger size on both sides of the perylene diimide core with high conjugated rigidity, so that the strong π - pi stacking effect of the perylene diimide core can be effectively inhibited, so that the molecule has aggregation-induced emission (AIE) property. The near-infrared two-region aggregation-induced light-emitting molecule and the amphiphilic lipid molecules DSPE-PEG5000 are self-assembled. The obtained water-soluble nanoparticles have good fluorescence intensity in the near-infrared two-region, imaging application in the near-infrared two-region can be realized, and the conjugated molecules also have good photothermal conversion efficiency and can be used for photothermal therapy of tumors.
Low dielectric dye type black matrix for color filter on array
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Paragraph 0049; 0140-0142, (2021/03/23)
The present invention relates to a low dielectric dye type black matrix for a color filter array structure. More specifically, the present invention relates to a tetrabenzoate (tetrabenzocorrolazine) dye having high color intensity, a broad absorption range, low dielectric and high durability, a photosensitive resin composition including the dye, a black matrix including the dye, and a color filter including the black matrix.
