Multibranched triarylamine end-capped triazines with aggregation-induced emission and large two-photon absorption cross-sections

Abstract

Multibranched triarylamine derivatives with a 1,3,5-triazine core have been synthesized and exhibit aggregation-induced emission and a large two-photon absorption cross section (8629 GM).

Starburst Triarylamine Donor–Acceptor–Donor Quadrupolar Derivatives Based on Cyano‐Substituted Diphenylaminestyrylbenzene: Tunable Aggregation‐Induced Emission Colors and Large Two‐Photon Absorption Cross Sections

“…[17] Recently, our group designed and synthesized multibranched triarylamine end-capped triazines that exhibit enhanced 2PA and AIE properties. [18] However, there are still few reports on dyes with high 2PA and AIE.…”

“…[10] Moreover, starburst triarylamine moieties as electron donors have better electron-donating and transporting capabilities, which may mean that the dyes have quite large two-photon activity because of the highly extended p conjugation and the appropriate intramolecular charge transfer (ICT); the introduction of the starburst triarylamine moiety is thus expected to exhibit the AIE phenomenon. [18,21] On the other hand, cyano-substituted compounds show good optical and electrical properties due to their high electron affinities. Molecules with an electron-withdrawing cyano group on the central phenylene ring are strongly fluorescent and have higher s values.…”

“…The precipitate was filtered off and washed with petroleum to give 12.9 g (84 %) of yellow solid. (2 a): Compound 1 (3 g, 5.7 mmol), diphenylamine (2.9 g, 17.1 mmol), copper powder (1.6 g, 25.7 mmol), potassium carbonate (6.76 g, 49.0 mmol), and [18]crown-6 (11.1 mg, 0.042 mmol) were heated in 1,2-dichlorobenzene (100 mL) at 180 8C for 48 h under an atmosphere of argon. The inorganic components were removed by filtration after cooling.…”

p-Carboxyl-N-salicylideneanilines: Simple but efficient chromophores for one-dimensional microrods with aggregation-induced emission enhancement (AIEE) characteristics

“…AIEE compounds such as silole derivatives [25][26][27], arylethene derivatives [28], 1-cyano-trans-1,2-bis(4 0 -methylbiphenyl)ethylene (CN-MBE) [29,30], and 1,4-di[(E)-2-phenyl-propenyl]benzene (PPB) [31] have been reported, and some of them have been successfully applied as fluorescence/biological probes and optoelectronic devices [32][33][34][35][36]. It is notable that the design principle for most AIEE compounds is mainly focused on the restriction of rotation of C-C single bond connecting two or more p-conjugated moieties [25][26][27][28][29][30][31][37][38][39][40][41][42].…”

Hexaphenylbenzene end-capped tri(p-phenylenevinylenes): synthesis and properties

“…Sonogashira coupling of 4-bromobenzaldehyde with phenylacetylene in the presence of a catalytic amount of PdCl 2 (PPh 3 ) 2 in dimethylformamide followed by Diels-Alder cycloaddition reaction with tetraphenyl-cyclopentadienone in diphenyl ether afforded 2 in 74% yield. HPB aldehyde derivatives 4 and 7 were synthesized from 3-iodo-4-methoxybenzaldehyde and 4-[bis-(4-iodophenyl)amino]benzaldehyde (5) 15 respectively, in good yield, using same reaction protocol. The synthetic route for targeted HPB-substituted trimers 9-11 is shown in Scheme 2.…”