19125-99-6Relevant articles and documents
Aggregation-induced emission or aggregation-caused quenching? Impact of covalent bridge between tetraphenylethene and naphthalimide
Ma, Xiaoxie,Chi, Weijie,Han, Xie,Wang, Chao,Liu, Shenghua,Liu, Xiaogang,Yin, Jun
, p. 1790 - 1794 (2021/03/08)
Understanding the physical mechanisms governing aggregation-induced-emission (AIE) and aggregation-caused-quenching plays a vital role in developing functional AIE materials. In this work, tetraphenylethene (TPE, a classical AIEgen) and naphthalimide (NI, a popular fluorophore with ACQ characteristics) were connected through non-conjugated linkages and conjugated linkages. We showed that the nonconjugated-linkage of TPE to NI fragments leads to substantial PET in molecular aggregates and ACQ. In contrast, the conjugated connection between TPE and NI moieties results in the AIE phenomenon by suppressing twisted intramolecular charge transfer. This work provides an important guideline for the rational design of AIE materials.
Efficient Intersystem Crossing in the Tr?ger's Base Derived From 4-Amino-1,8-naphthalimide and Application as a Potent Photodynamic Therapy Reagent
Barbon, Antonio,Chen, Kepeng,Hou, Yuqi,Li, Shujing,Wang, Zhijia,Wu, Huijian,Yaglioglu, Halime Gul,Yildiz, Elif Akhuseyin,Zhang, Xue,Zhao, Jianzhang,Zhao, Yingjie
, (2020/03/05)
Intersystem crossing (ISC) was observed for naphthalimide (NI)-derived Tr?ger's base, and the ISC was confirmed to occur by a spin-orbital charge-transfer (SOCT) mechanism. Conventional electron donor/acceptor dyads showing SOCT-ISC have semirigid linkers. In contrast, the linker between the two chromophores in Tr?ger's base is rigid and torsion is completely inhibited, which is beneficial for efficient SOCT-ISC. Femtosecond transient absorption (TA) spectra demonstrated charge-separation and charge-recombination-induced ISC processes. Nanosecond TA spectroscopy confirmed the ISC, and the triplet state is long-lived (46 μs, room temperature). The ISC quantum yield is dependent on solvent polarity (8–41 %). The triplet state was studied by pulsed-laser-excited time-resolved EPR spectroscopy, and both the NI-localized triplet state and triplet charge-transfer state were observed, which is in good agreement with the spin-density analysis. The Tr?ger's base was confirmed to be a potent photodynamic therapy reagent with HeLa cells (EC50=5.0 nm).
Photophysics, Electrochemistry, Morphology, and Bioimaging Applications of New 1,8-Naphthalimide Derivatives Containing Different Chromophores
Saini, Ankita,Thomas, K. R. Justin,Sachdev, Abhay,Gopinath, Packirisamy
, p. 2612 - 2622 (2017/10/07)
A series of 1,8-naphthalimide-based fluorophores containing different chromophores with varying conjugation and electron richness at the imidic nitrogen atom are synthesized and characterized. These amine-functionalized naphthalimides are bipolar in nature and exhibit interesting optical and morphological variations attributable to the nature of the N substituents. Despite the fact that the dyes are structurally different owing to variation of the substituent on the imidic nitrogen atom, their electronic characteristics are similar and originate from the 4-aminonaphthalimide segment. Nevertheless, they exhibit variations in morphology in the microscopic domain, and this is attributable to structural differences. Further, these fluorescent dyes display biocompatibility and are used in the bioimaging of cells.
