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

Hongkun Li; Xiaoyan Zheng; Huimin Su; Jacky W.Y. Lam; Kam Sing Wong; Shan Xue; Xuejiao Huang; Xuhui Huang; Bing Shi Li; Ben Zhong Tang

doi:10.1038/srep19277

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

Hongkun Li, Xiaoyan Zheng, Huimin Su, Jacky W.Y. Lam, Kam Sing Wong, Shan Xue, Xuejiao Huang, Xuhui Huang, Bing Shi Li^*, Ben Zhong Tang

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

69 Citations (Scopus)

Abstract

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, €- € interactions and steric effect.

Original language	English
Article number	19277
Journal	Scientific Reports
Volume	6
DOIs	https://doi.org/10.1038/srep19277
Publication status	Published - 13 Jan 2016
Externally published	Yes

Access to Document

10.1038/srep19277

Cite this

@article{0edbf686309a4d0ea3c96ec254d485d5,

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

abstract = "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, €- € interactions and steric effect.",

author = "Hongkun Li and Xiaoyan Zheng and Huimin Su and Lam, {Jacky W.Y.} and {Sing Wong}, Kam and Shan Xue and Xuejiao Huang and Xuhui Huang and Li, {Bing Shi} and Tang, {Ben Zhong}",

year = "2016",

month = jan,

day = "13",

doi = "10.1038/srep19277",

language = "English",

volume = "6",

journal = "Scientific Reports",

issn = "2045-2322",

publisher = "Nature Publishing Group",

}

TY - JOUR

T1 - Synthesis, optical properties, and helical self-assembly of a bivaline-containing tetraphenylethene

AU - Li, Hongkun

AU - Zheng, Xiaoyan

AU - Su, Huimin

AU - Lam, Jacky W.Y.

AU - Sing Wong, Kam

AU - Xue, Shan

AU - Huang, Xuejiao

AU - Huang, Xuhui

AU - Li, Bing Shi

AU - Tang, Ben Zhong

PY - 2016/1/13

Y1 - 2016/1/13

N2 - 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, €- € interactions and steric effect.

AB - 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, €- € interactions and steric effect.

UR - http://www.scopus.com/inward/record.url?scp=84955323397&partnerID=8YFLogxK

U2 - 10.1038/srep19277

DO - 10.1038/srep19277

M3 - Article

AN - SCOPUS:84955323397

SN - 2045-2322

VL - 6

JO - Scientific Reports

JF - Scientific Reports

M1 - 19277

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this