Tetraphenylethene-Functionalized Conjugated Helical Poly(phenyl isocyanide) with Tunable Light Emission, Assembly Morphology, and Specific Applications

Abstract

Aggregation-induced emission (AIE) active tetraphenylethene (TPE) functionalized phenyl isocyanide (PI) derivatives, such as TPE pendent PI monomers (TPE-NC) and TPE-based Pd­(II) catalysts (TPE-Cat. a and TPE-Cat. b) were synthesized. The corresponding linear (poly­(TPE-NC) n ) and four-armed (TPE-[poly­(TPE-NC) m ]4) conjugated polymers were subsequently prepared through the living polymerization of TPE-NC with TPE-Cat. a or TPE-Cat. b in THF, respectively. All of them have good solubility in common organic solvents, such as THF and CHCl3, and exhibited tunable AIE property, which can be facilely tuned through the variations on the concentration and the molecular weights (MWs) of the polymers. They also showed excellent thermal stability with a 5% of their weight loss as high as 380–405 °C and significant mass loss in the range of 350–650 °C. Stable helical assemblies could be formed by poly­(TPE-NC)n at high concentration conditions. However, four-armed TPE-[poly­(TPE-NC) m ]4 could self-assemble into an apparent bumpy “caterpillar” like assembly, which was very different from the ordinary ones. Moreover, these conjugated polymers could be employed to generate a vapochromism phenomenon and act as good dispersants for carbon agglomerates in poor solvents. It is expected that this work can enrich the family of luminescent materials based on the helical poly­(phenyl isocyanide) main chains and guide the future design of optical materials with attractive structures and special purposes, such as heat-resistant materials, security materials, and dispersed materials.

Highly enantioselective photo-polymerization enhanced by chiral nanoparticles and in situ photopatterning of chirality

“…4 . In the past decades, many strategies have been developed to synthesize chiral conjugated polymers 5 , typically using chiral monomers 6 , dopants, catalysts 7 , or asymmetric external influences including circularly polarized light (CPL) 8,9 , vortex motion 10 , stirring 11 and other physical forces 12 , as the symmetry breaker.…”

An acrylate AIE-active dye with a two-photon fluorescent switch for fluorescent nanoparticles by RAFT polymerization: synthesis, molecular structure and application in cell imaging

“…The pure product was obtained by drying under vacuum, which was named as TPEOM (0.808 g, 66% yield). 1…”

“…Finally, the product was chromatographed on a silica gel column using n-hexane/ dichloromethane (v/v ¼ 2 : 1) as mobile phase, which was further dried under vacuum and named as TPEOH (0.532 g, 68% yield). 1…”

“…Among them, organic uorescent materials have designable and variable structures with excellent optical performance, which has attracted the extensive attention of a large number of researchers. [1][2][3] In 2001, the wonderful phenomenon of aggregation-induced emission (AIE) was discovered by Tang's group, which has attracted the extensive interest of many researchers. 4 The AIE phenomenon refers to the fact that some molecules do not emit uorescence or emit very weak uorescence in good solvents, but emit uorescence or stronger uorescence in the aggregated state, which is completely contrary to the aggregation-caused quenching (ACQ) phenomenon of traditional organic uorescent materials in an aggregated state.…”

Cross‐linking induced thermoresponsive hydrogel with light emitting and self‐healing property

“…On the other side, the aggregation‐induced emission (AIE) property of the fluorescent substances could be an alternative based on enhanced emission at aggregation state . The AIE property of TPE was proposed by Professor Tang in 2001 and drew great attentions as bioimaging probes in recent years . At the same time, the researchers began to study the TPE containing hydrogels in recent years, the salt‐responsive luminescent hydrogel and light‐emitting hydrogels containing chitosan were reported by Liang group and Tang group .…”