Aggregation-induced chirality, circularly polarized luminescence, and helical self-assembly of a leucine-containing AIE luminogen

Li, Hongkun; Cheng, Juan; Deng, Haiqin; Zhao, Engui; Shen, Bo; Lam, Jacky W. Y.; Wong, Kam Sing; Wu, Hongkai; Li, Bing Shi; Tang, Ben Zhong

doi:10.1039/c4tc02726d

Cited by 118 publications

(62 citation statements)

References 54 publications

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“…It is believed that the twisted ribbonsb raid together to form helical fibers (Figure S11i nt he Supporting Information). [20] TEM data confirmed the self-assembly of the aggregates. Branching in the leaf-shapeda ggregates of PM2 can be visual-ized in Figure 8b and da nd Figure S11b and di nt he Supporting Information.…”

Section: Aggregate Morphologysupporting

confidence: 55%

Exquisite 1D Assemblies Arising from Rationally Designed Asymmetric Donor–Acceptor Architectures Exhibiting Aggregation‐Induced Emission as a Function of Auxiliary Acceptor Strength

Singh

Mukhopadhyay

Biswas

et al. 2015

Chemistry A European J

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One-dimensional nanostructures with aggregation-induced emission (AIE) properties have been fabricated to keep the pace with growing demand from optoelectronics applications. The compounds 2-[4-(4-methylpiperazin-1-yl)benzylidene]malononitrile (PM1), 2-{4-[4-(pyridin-2-yl)piperazin-1-yl]-benzylidene}malononitrile (PM2), and 2-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]benzylidene}malononitrile (PM3) have been designed and synthesized by melding piperazine and dicyanovinylene to investigate AIE in an asymmetric donor-acceptor (D-A) construct of A'-D-π-A- topology. The synthetic route has been simplified by using phenylpiperazine as a weak donor (D), dicyanovinylene as an acceptor (A), and pyridyl/pyrimidyl groups (PM2/PM3) as auxiliary acceptors (A'). It has been established that A' plays a vital role in triggering AIE in these compounds because the same D-A construct led to aggregation-caused quenching upon replacing A' with an electron-donating ethyl group (PM1). Moreover, the effect of restricted intramolecular rotation and twisted intramolecular charge transfer on the mechanism of AIE has also been investigated. Furthermore, it has been clearly shown that the optical disparities of these A'-D-π-A architectures are a direct consequence of comparative A' strength. Single-crystal X-ray analyses provided justification for role of intermolecular interactions in aggregate morphology. Electrochemical and theoretical studies affirmed the effect of the A' strength on the overall properties of the A'-D-π-A system.

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Section: Aggregate Morphologysupporting

confidence: 55%

Exquisite 1D Assemblies Arising from Rationally Designed Asymmetric Donor–Acceptor Architectures Exhibiting Aggregation‐Induced Emission as a Function of Auxiliary Acceptor Strength

Singh

Mukhopadhyay

Biswas

et al. 2015

Chemistry A European J

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“…We thuss ynthesized two mono-substituted chiral TPE derivatives with lvaline-and l-leucine-containinga ttachments 6 and 7 (Figure 3), respectively. [43,44] To investigate the influence of the number of chiral attachments on their self-assembly and luminescencep roperties, we then prepared two substituted chiral TPE derivatives 8 and 9 carrying bivaline and bileucinea ttachments, respectively. [45,46] Apart from the TPE-based AIEgens with point chirality,A IEgens 10-12 with axial chirality were synthesized by modifyingT PE units with an axial chiral moiety, binaphthol.…”

Section: Tpe Derivativesmentioning

confidence: 99%

“…SEM(a) and TEM (b) images of the aggregates of 6 formedu pon evaporation of DCE/hexanesolution (1:9, v/v), [6] = 10 À4 m.S EM (c)and fluorescence microscopy (d) images of the aggregates of 7 formed upon evaporation of DCE/hexane solution (1:9, v/v), [7] = 10 À4 m.R eprinted with permission from refs [43]. and[44].Copyright 2014 and 2015, Royal Societyof Chemistry.…”

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confidence: 99%

Molecular Design, Circularly Polarized Luminescence, and Helical Self‐Assembly of Chiral Aggregation‐Induced Emission Molecules

Tang

2019

Chemistry An Asian Journal

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Aggregation‐induced emission luminogens (AIEgens) are a new class of luminophors, which are non‐emissive in solution, but emit intensively upon aggregation. By properly designing the chemical structures of the AIEgens, their aggregation process can be tuned towards a desired direction to give diverse novel luminescent architectures of micelles, rods, and helical fibers. AIEgens represent a kind of promising building block for the fabrication of luminescent micro/nanostructures with controllable morphologies. In this review, we describe our recent work in this research area, focusing on the molecular design, circularly polarized luminescence properties, and helical self‐assembly behavior of AIEgens.

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“…Proteins form helical conformation and super-helical assemblies, which are induced by the chiral centres in their amino acid sequence. Inspired by the structural codes of amino acids, we have recently introduced an amino acid pendant into TPE scaffold and synthesized chiral TPE derivatives 28 29 . The molecules are found to assemble into helical micro/nanofibers emitting circularly polarized light.…”

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confidence: 99%

Synthesis, optical properties and helical self-assembly of a bivaline-containing tetraphenylethene

Zheng

et al. 2016

Sci Rep

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A chiral tetraphenylethene derivative with two valine-containing attachments (TPE-DVAL), was synthesized by Cu(I)-catalyzed azide-alkyne “click” reaction. The optical properties and self-assembling behaviours of TPE-DVAL were investigated. The molecule is non-emissive and circular dichroism (CD)-silent in solution, but shows strong fluorescence and Cotton effects in the aggregation state, demonstrating aggregation-induced emission (AIE) and CD (AICD) characteristics. TPE-DVAL exhibits good circularly polarized luminescence (CPL) when depositing on the surface of quartz to allow the evaporation of its 1,2-dichloroethane solution. SEM and TEM images of the molecule show that the molecule readily self-assembles into right-handed helical nanofibers upon the evaporation of its solvent of DCE. The molecular alignments and interactions in assembling process are further explored through XRD analysis and computational simulation. The driving forces for the formation of the helical fibers were from the cooperative effects of intermolecular hydrogen bonding, π-π interactions and steric effect.

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Aggregation-induced chirality, circularly polarized luminescence, and helical self-assembly of a leucine-containing AIE luminogen

Abstract: TPE-Leu, an AIE luminogen, shows aggregation-induced chirality, and can self-assemble into helical micro/nanofibers, displaying good circularly polarized luminescence performance.

Cited by 118 publications

References 54 publications

Exquisite 1D Assemblies Arising from Rationally Designed Asymmetric Donor–Acceptor Architectures Exhibiting Aggregation‐Induced Emission as a Function of Auxiliary Acceptor Strength

Exquisite 1D Assemblies Arising from Rationally Designed Asymmetric Donor–Acceptor Architectures Exhibiting Aggregation‐Induced Emission as a Function of Auxiliary Acceptor Strength

Molecular Design, Circularly Polarized Luminescence, and Helical Self‐Assembly of Chiral Aggregation‐Induced Emission Molecules

Synthesis, optical properties and helical self-assembly of a bivaline-containing tetraphenylethene

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