Effect of AIE Substituents on the Fluorescence of Tetraphenylethene-Containing BODIPY Derivatives

Abstract

A series of BODIPY derivatives with tetraphenylethene (TPE) moieties were designed and synthesized. The effect of positions and numbers of substitution groups on the fluorescence of the BODIPYs was investigated. Theoretical calculation and single crystal structures proved that the TPE substitution groups on the 8-position of BODIPY contributed little to the conjugation, but benefited the aggregated state emission. On the other hand, the substitutions on the 3- or 5-position of BODIPY through vinyl bridges increased the conjugation length, and generated big coplanar π-conjugated structures with poor aggregated state emission. The compound with bright aggregated state emission has been further fabricated into biocompatible fluorescent nanoparticles and used as effective fluorescent contrast agents for intracellular imaging.

Aggregation-induced emission enhancement and cell imaging of a novel (carbazol-N-yl)triphenylamine–BODIPY

“…It can be clearly seen that two major absorption bands are located at 320 nm and 500 nm. What is interesting is that the emission spectrum of BCPA-BODIPY has two peaks, a relatively stronger emission peak at 520 nm and a weaker red fluorescence peak at 656 nm, the former which is similar with that of parent BODIPY is the typical LE emission peak of BODIPY core and the latter which has unstructured luminescence spectrum is a new twisted intramolecular charge transfer (TICT) peak 6,[18][19][20] .…”

Synthesis and assembly of polyhedral oligomeric silsesquioxane end-capped amphiphilic polymer to enhance the fluorescent intensity of tetraphenylethene

“…When fluorescent molecules are aggregated, their light emission will be partially or completely quenched [26][27][28]. In contrast, tetraphenylethene (TPE) shows non-fluorescence in good solvent but emit strong fluorescence in aggregated state due to the restriction of intramolecular rotation (RIR) [29][30][31][32][33] far, TPE has been widely studied for applications such as bioimaging [34,35], specific detection [36][37][38][39], gene and drug delivery [40,41] and biosensors [42]. In this study, POSS-b-PDMAEMA-b-PMMAwas prepared by atom transfer radical polymerization (ATRP) and the selfassembling behaviours of the copolymer in different solvents were investigated.…”

Asymmetric Difluoroboron Quinazolinone‐Pyridine Dyes with Large Stokes Shift: High Emission Efficiencies Both in Solution and in the Solid State

“…For 6-halogens ubstituted BODIQPys,t he heavy atomic effect of bromine and iodine was suppressed in solution due to the strong electron-withdrawing ability of the BODIQPy core. [17] Herein, we report the facile synthesis and fluorescence properties of asymmetric difluoroboronq uinazolinone-pyridine complexes( BODIQPys), which exhibit ultra-high emissione fficiencies with particularly high Stokes shifts both in solution and in the solid state. In the solid state, the asymmetric structurei nducedaunique dimeric structure, and efficient luminescence was also observed.…”

“…[5] But two deficiencieso fBODIPY dyes are their generally small Stokess hift (5-20 nm, in most cases) [6] andl ow fluorescencei n the solid state. [17] Herein, we report the facile synthesis and fluorescence properties of asymmetric difluoroboronq uinazolinone-pyridine complexes( BODIQPys), which exhibit ultra-high emissione fficiencies with particularly high Stokes shifts both in solution and in the solid state. However, most of them exhibit weak or quenched fluorescencei nt he solid state due to the aggregation-caused quenching( ACQ).…”

“…[14] However,t he fluorescenceofthose compounds with AIE properties is usually weak in solution. [17] Herein, we report the facile synthesis and fluorescence properties of asymmetric difluoroboronq uinazolinone-pyridine complexes( BODIQPys), which exhibit ultra-high emissione fficiencies with particularly high Stokes shifts both in solution and in the solid state. [9,16] Until now,t ot he best of our knowledge,t he difluoroboron complexesw ith high effective emission both in solution and solid state were rare.…”