Solvent‐Dependent Nanostructures Based on Active π‐Aggregation Induced Emission Enhancement of New Carbazole Derivatives of Triphenylacrylonitrile

Abstract

In the present study, the carbazole and 2,3,3‐triphenylacrylonitrile (TPAN) nanostructures (2‐CTPAN and 2,2′‐CTPAN) have been designed and synthesized by Pd‐catalyzed Sonogashira cross‐coupling reaction. CTPAN exhibit aggregation‐induced emission enhancement (AIEE) behavior in water with high fluorescence quantum yield. Both the compounds show tunable self‐assembly in water as well as in N,N‐dimethylformamide (DMF) by extended π–π stacking interactions. CTPAN can be self‐assembled into spherical particles in water and the structures of these self‐assemblies have been investigated using X‐ray diffraction. Interestingly, 2‐CTPAN and 2,2′‐CTPAN form organogels with a critical gelation concentration (CGC) of 11 and 15 mg mL−1, respectively, in DMF and exhibit acicular and rod shaped morphology, respectively. The single‐crystal structure of 2‐CTPAN shows that the intermolecular C−H⋅⋅⋅π interactions lock the molecular conformation into a staircase‐shaped supramolecular assembly. These AIEE active compounds reveal high water dispersibility, strong yellow fluorescence with high quantum yield, promising photostability and excellent biocompatibility, which make them potential bioimaging agents.

Bicarbazole‐based oxalates as photoinitiating systems for photopolymerization under UV–Vis LEDs

“…As a chromophore with rigid π‐conjugated planes, carbazole and its derivatives have potential applications as good PIs with excellent photoelectric properties and electron delocalization . Xu et al designed and synthesized a series of carbazole‐based oxime ester (OXE) PIs that exhibit excellent photoinitiating properties with a maximum absorption of 330 nm.…”

Towards Blue AIE/AIEE: Synthesis and Applications in OLEDs of Tetra-/Triphenylethenyl Substituted 9,9-Dimethylacridine Derivatives

“…Compounds based on carbazole [17][18][19] or triphenylamine [20,21] moieties substituted by tetraphenylethene and/or triphenylethene units were previously reported to show AIE or AIEE effects. Due to the specific linkage topology, some of them displayed blue/sky-blue fluorescence [22,23].…”

Oligosilanyl-Bridged Biscarbazoles: Structure, Synthesis, and Spectroscopic Properties

“…13 Carbazole derivatives are usually employed as an electronic-donor group and they exhibit good absorption and fluorescence. 14,15 Until now, research on carbazole derivatives focuses on π−π orbital interaction, and so far, only one study on carbazolyl−arysilane connected by the N−Si bond has been reported for OLEDs and its structure/ property relationships have not been fully explored. 16,17 Moreover, no conjugated molecules containing a carbazolyl group and Si bridged by the C−Si bond have ever been reported before.…”

“…Carbazole-based compounds have attracted considerable attention as hole-transporting and light-emitting materials in scientific and industrial fields . Carbazole derivatives are usually employed as an electronic-donor group and they exhibit good absorption and fluorescence. , Until now, research on carbazole derivatives focuses on π–π orbital interaction, and so far, only one study on carbazolyl–arysilane connected by the N–Si bond has been reported for OLEDs and its structure/property relationships have not been fully explored. , Moreover, no conjugated molecules containing a carbazolyl group and Si bridged by the C–Si bond have ever been reported before. Understanding the effect of the smallest electronic building blocks represents a crucial step toward the development of new functionalized materials.…”