548-35-6Relevant articles and documents
Design and synthesis of highly twisted phenanthroimidazole substituted blue-emitting truxene based fluorescent chromophores
Kaur, Banpreet,Moghe, Dhanashree,Kabra, Dinesh,Jacob, Josemon
, p. 2278 - 2288 (2019)
The modified Debus-Radziszewski reaction was used to design and synthesize novel truxene derived blue-emitting materials bearing phenanthroimidazole substituents. The materials were prepared non-catalytically under ambient conditions using a triamino based derivative of truxene as a key precursor in good yields. The 5, 5′, 10, 10′, 15, and 15′ positions of the truxene were alkylated to provide solubility to the molecules, making the materials solution processable. The substituted phenanthroimidazole moieties were introduced at the 2, 7, 12 positions of truxene to synthesize the target molecules. Three new materials were prepared by varying the phenyl group attached at the C2 position of the phenanthroimidazole moiety, designated as PT1 for the phenyl, PT2 for the 4-methoxyphenyl, and PT3 for the 4-cyanophenyl substituent. From the photophysical studies, PT3 was found to have dominant charge transfer characteristics in its excited state. Also, PT3 exhibited a photoluminescence quantum yield as high as 0.83. The optimized geometries from the computational studies revealed that the molecules are highly twisted, with dihedral angles of ～75°. The HOMO-LUMO distributions were found to be well separated showing the bipolar characteristic of the compounds. The band gap values from computational studies were found to be in agreement with experimental values. The emission spectra in the solid state gave maxima at 402 nm for PT1, 412 nm for PT2, and 450 nm for PT3. The materials were thus found to be emitting in the blue region of the visible spectrum. The TCSPC and TRPL studies were carried out to explore further the excited states of the molecules, wherein radiative pathways were found to be dominant.
Acceptor or donor (diaryl B or N)substituted octupolar truxene: Synthesis, structure, and charge-transfer-enhanced fluorescence
Yuan, Mao-Sen,Fang, Qi,Liu, Zhi-Qiang,Guo, Jian-Ping,Chen, Hong-Yu,Yu, Wen-Tao,Xue, Gang,Liu, Dian-Sheng
, p. 7858 - 7861 (2006)
(Graph Presented) Two diaryl B- and N-substituted truxene charge-transfer compounds B3 and N3 have been synthesized. The fluorescence intensities of several nonfunctionalized truxene compounds are 1 order of magnitude weaker than that of B3 and N3. To reveal the structure-property correlations, the X-ray structures of B3 and N3 and their precursors 3 and 4 have been determined. The extended molecular dimension, the especially shortened B-C bond, and the improved planarity of B3 can serve as direct structural evidence for the charge transfer.
Cost-effective hole transporting material for stable and efficient perovskite solar cells with fill factors up to 82%
Guan, Lei,Yin, Xinxing,Zhao, Dewei,Wang, Changlei,An, Qiaoshi,Yu, Jiangsheng,Shrestha, Niraj,Grice, Corey R.,Awni, Rasha A.,Yu, Yue,Song, Zhaoning,Zhou, Jie,Meng, Weiwei,Zhang, Fujun,Ellingson, Randy J.,Wang, Jianbo,Tang, Weihua,Yan, Yanfa
, p. 23319 - 23327 (2017)
A new small molecule-based hole selective material (HSM), 4,4′,4′′-(7,7′,7′′-(5,5,10,10,15,15-hexahexyl-10,15-dihydro-5H-diindeno[1,2-a:1′,2′-c]fluorene-2,7,12-triyl)tris(2,3-dihydrothieno[3,4-b][1,4]dioxine-7,5-diyl))tris(N,N-bis(4-methoxyphenyl)aniline) (TRUX-E-T), has been developed by a facile synthesis with reduced cost. The highest occupied molecular orbital energy level and lowest unoccupied molecular orbital energy level of TRUX-E-T are -5.10 and -2.50 eV, respectively, making it a suitable HSM for lead iodide perovskite solar cells. TRUX-E-T can be smoothly deposited onto perovskite layers, enabling efficient perovskite solar cells with thin TRUX-E-T layers (～50 nm), which helps cut the unit cost of the HSL used in PVSCs to approximately one-fortieth (1/40) of 2,2′,7,7′-tetrakis (N,N-di-p-methoxyphenylamino)-9,9′-spirobifluorene (spiro-OMeTAD). Additionally, TRUX-E-T exhibits hole mobilities as high as 2.47 × 10-4 cm2 V-1 s-1, better than spiro-OMeTAD. As a result, our perovskite solar cells using TRUX-E-T have shown high fill factors up to 82%. The champion cell achieved a maximum power conversion efficiency of 18.35% (16.44%) when measured under reverse (forward) voltage scan under AM1.5 G 100 mW cm-2 illumination. Our un-encapsulated cells exhibited good stability in ambient air, maintaining 96.4% of their initial efficiency of 18.35% after 20 days of storage.
A Case Study on the Influence of Substitutes on Interlayer Stacking of 2D Covalent Organic Frameworks
Fan, Yu,Wen, Qiang,Zhan, Tian-Guang,Qi, Qiao-Yan,Xu, Jia-Qiang,Zhao, Xin
, p. 5668 - 5672 (2017)
Interlayer stacking of 2D covalent organic frameworks (COFs) plays a crucial role in determining not only the geometry of channels inside COFs but also the mobility of carrier transport between COF layers. However, though topological structures of 2D COFs monolayers can be precisely predicted through the structures of building blocks, factors affecting their interlayer stacking remain poorly understood. In this work, a truxene-based building block on which six methyl groups are introduced was designed. The condensation of it with 1,4-diaminobenzene or benzidine afforded 2D COFs with the methyl groups extending out-of-plane of the layers. A significant influence of the methyl groups on interlayer stacking of the COFs was revealed by the adoption of inclined packing of monolayers, which has never been experimentally observed before. This unprecedented stacking manner was confirmed by powder X-ray diffraction analysis, pore-size distribution analysis, and TEM investigation.
Synthesis of new truxene derivatives: Possible precursors of fullerene partial structures?
Dehmlow, Eckehard V.,Kelle, Torsten
, p. 2021 - 2031 (1997)
Preparations of compound 4 and of truxene derivatives 5, 6a,b, 7, 8, 10a,b, 11, 12a,b, and 13a,b are described. These substances are potential starting materials for the synthesis of bowl shaped polyaromatic compounds containing structural elements of fullerenes.
Effective blocking of the molecular aggregation of novel truxene-based emitters with spirobifluorene and electron-donating moieties for furnishing highly efficient non-doped blue-emitting OLEDs
Yao, Chunliang,Yu, Yue,Yang, Xiaolong,Zhang, Huiming,Huang, Zuan,Xu, Xianbin,Zhou, Guijiang,Yue, Ling,Wu, Zhaoxin
, p. 5783 - 5794 (2015)
Several truxene-based blue fluorescent emitters bearing different functional moieties and peripheral spirobifluorene groups have been successfully designed and synthesized. Through tuning the chemical structures and electronic characters of the functional moieties, both optimized molecular configuration and elevated highest occupied molecular orbital (HOMO) energy levels have been afforded to the truxene-based emitters, representing a new effective strategy for solving the problems of molecular aggregation and poor charge carrier injection/transport associated with the truxene-based blue emitters. Owing to the sophisticated strategy, the concerned emitters can furnish highly efficient non-doped blue-emitting OLEDs with a maximum current efficiency (ηL) of 7.41 cd A-1, an external quantum efficiency (ηext) of 4.33%, and a power efficiency (ηP) of 6.79 lm W-1, representing the state-of-the-art EL efficiencies ever achieved by the truxene-based blue emitters. All promising results will not only show the great potential of the concerned truxene-based blue fluorescent emitters in the field of OLEDs, but also furnish valuable clues for developing high-performance truxene-based emitters.
C 3-Symmetric star shaped donor-acceptor truxenes: Synthesis and photophysical, electrochemical and computational studies
Sharma, Rekha,Maragani, Ramesh,Misra, Rajneesh
, p. 882 - 890 (2018)
This manuscript reports the design and synthesis of C3-symmetric star shaped donor and acceptor substituted truxenes 6, 7, 10 and 11 using Pd-catalyzed Sonogashira cross-coupling and [2+2] cycloaddition-retroelectrocyclization reactions. Their photophysical, electrochemical and computational studies were explored, which indicate strong donor-acceptor interactions and effective tuning of the HOMO-LUMO gap. The computational studies reveal that the TCNE and TCNQ substituted truxenes 10 and 11 exhibit lower HOMO-LUMO gaps compared to truxenes 6 and 7. The reaction pathway of [2+2] cycloaddition-retroelectrocyclization was studied using computational calculations, which reveal that the donor substituted truxene 7 is favourable for cycloaddition-retroelectrocyclization reactions, whereas acceptor substituted truxene 6 is not favourable.
Star-shaped electron acceptors containing a truxene core for non-fullerene solar cells
Lin, Kaiwen,Xie, Boming,Wang, Zhenfeng,Xie, Ruihao,Huang, Yunping,Duan, Chunhui,Huang, Fei,Cao, Yong
, p. 42 - 50 (2018)
A series of new electron acceptors containing a truxene core with intense optical absorption were synthesized and used for non-fullerene organic solar cells. Due to the weak electron-donating characteristic of truxene core and thereby weak intramolecular charge transfer interaction from electron-donating core to electron-withdrawing end groups, the resulting new acceptors show relatively wide optical band-gap and high-lying lowest unoccupied molecular orbitals (LUMOs), which consequently lead to complementary light spectra with narrow band-gap donor polymers and high open circuit voltage (Voc) in solar cells. Particularly, Tr(Hex)6-3BR, a star-shaped planar acceptor, produced the highest power conversion efficiency of 2.1% with a high Voc of 1.02 V when blended with PTB7-Th.
A simple synthesis of truxene, a building block for optoelectronics and fullerene fragments
Oded, Yaacov Netanel,Agranat, Israel
, p. 636 - 638 (2014)
Truxene was efficiently synthesized by reduction of truxenone with excess hydrazine hydrate in diethylene glycol at 180 C without added base, a variation of the Huang-Minlon Wolff-Kishner reduction. The proposed mechanism highlights hydrazine as a nucleophile and a base, extracting protons from the hydrazone and diazene intermediates.
Star-shaped oligofluorene truxene macromolecules - Synthesis and properties as a function of alkyl chain length
Kanibolotsky, Alexander L.,Orofino, Clara,Skabara, Peter J.
, (2021/11/26)
Star-shaped oligofluorene truxenes are very promising materials and have demonstrated excellent properties as the gain medium in organic semiconductor lasers (OSLs).1-10 Alkyl chains in oligofluorene truxenes act as solubilizing groups as well as spacers to prevent intermolecular π-π stacking that leads to quenching of the light emission. A new series of star-shaped systems analogous to hexyl oligofluorene truxenes11 with alkyl chains of different lengths (butyl chains and octyl chains) was synthesized. The objective of this study was to investigate the effect of alkyl chain length on the film-forming properties of oligofluorene-truxene materials and, as a result, on their optoelectronic properties for applications as the gain medium in OSLs.
Gas transport properties of truxene-based network polyimide membrane with flexible hexyl side chains
Liu, Xiangyun,Luo, Jiangzhou,Wang, QingQing,Xue, Song,Zong, Xueping
, (2021/11/11)
Crosslinking is a viable way to construct the network polymers which possesses the merits of high rigidity, excellent plasticization resistances, and good thermal stability using in the area of gas separation. However, dependence on crosslinking method often leads to contracted pores among polymer chains and in turn, sacrifices gas permeability seriously. In this work, a novel truxene triamine monomer with flexible hexyl side chains (termed as HTUTA) was designed, synthesized, and subsequently reacted with three different dianhydrides ODPA, BTDA, and 6FDA though polycondensation to obtain a series of network polyimides (PIs) membranes. Among these three designed truxene-based network PIs, HTUTA-6FDA had the best overall gas separation performance rooting from its bulky –C(CF3)2- moieties within the polymer framework. Compared with our previous reported TAPA-6FDA and TAPB-6FDA, the overall gas transport properties of the newly designed truxene-based network PIs are enhanced obviously because of incorporating the bulky and flexible side chains as well as enhancing the polymer backbone rigidity via using the truxene structure as the building block. For instance, the gas permeability of designed HTUTA-6FDA for CO2 and O2 were, respectively, enhanced 261% and 253% in comparison with these of TAPB-6FDA. In addition, benefiting from the flexible hexyl side chains, the partial chain segment motion was increased and accordingly the inter- and intra-chain interactions were minimized. Thus, a broad operating flexibility without the risk of gelation could be achieved during the tridimensional polycondensation process, which is extremely significant to their practical production. We hope this study can open a new insight into the rational design of the network PI membranes with enhanced gas permeability as well as no risk of gelation trend before film-forming.
