Aggregation-induced emission and reversible mechanochromic luminescence of carbazole-based triphenylacrylonitrile derivatives

Abstract

Conjugated organic molecules exhibiting AIE are characterized by the strongly twisted conjugated skeleton, which could provide loose intermolecular stacking and weak π–π interactions in the solid state to generate stimuli-responsive materials.

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

“…2,3,3-Triphenylacrylonitrile (TPAN) was selected as AIE molecule because this molecule was well studied and various chemical functionalization methods could be easily performed. [40,41] Chemical structure of the probes( Scheme 1) and details of the synthesis approacha re shown in Scheme S1 (see the Supporting Information). Chemical structures and purities of 2-CTPAN and 2,2'-CTPAN were fully established and confirmed by 1 HNMR, 13 CNMR and HRMS analyses (Figure S1-S6).…”

“…2,3,3‐Triphenylacrylonitrile (TPAN) was selected as AIE molecule because this molecule was well studied and various chemical functionalization methods could be easily performed . Chemical structure of the probes (Scheme ) and details of the synthesis approach are shown in Scheme S1 (see the Supporting Information).…”

“…This indicates as ignificant AIEE effect and as trong yellow fluorescencea ppearsd ue to lowering of the solubility of the FONs in the solution.T he quantum yield (f f )o f2 -CTPAN and 2,2'-CTPAN are calculated using quininesulfate as standard (in 0.1 m H 2 SO 4 , f f = 54 %). [41,45] The f f of 2-CTPAN in 0a nd 99 % H 2 O/THF are 0.52 and 7.55 %, respectively,w hereas the f f of 2,2'-CTPAN in 0a nd 99 %H 2 O/THF are 0.36 and 13.52 %, respectively.T hese resultsc learly demonstrate that 2-CTPAN and 2,2'-CTPAN exhibit AIEE properties.…”

“…[40] Zhan et al studied AIE, ICT and mechanofluorochromic properties of carbazole-based triphenylacrylonitriled erivatives. [41] Herein, we present the design and synthesis of substituted carbazole-TPAN based dyes (2-CTPAN and 2,2'-CTPAN) and their AIEE characteristics. The photophysical and self-assembly behavioro ft he dyes have been investigated in detail.…”

Disparity in piezofluorochromism for twisted mono-carbazole-based AIEgens resulting from interchanging electron-rich substituents: effect of coplanarity on twisted π-conjugates

“…9a-f Carbazole-based D-p-A systems 11a,b,10 and dendrons with multiple carbazole units have been judiciously designed, but only a few of them display a marginal PFC behavior. 12 Difficulties in switching from the crystalline to the amorphous state under pressure result in a barrier. The polymeric material embedded with carbazole offered mechanofluorochromic (MFC) properties, but the elusive and complicated molecular structure of the polymeric material is a disadvantage.…”