Chiral tether-guided selective synthesis of <i>D</i> <sub> <i>n</i> </sub> -symmetric chiral conjugated nanorings

Chiral conjugated nanorings with <i>D</i> <sub><i>n</i></sub> symmetry exhibit extraordinary circularly polarized luminescence (CPL) properties due to their unique cylindrical helical conjugated system. However, their synthesis faces challenges such as numerous atropisomers and tedious separation and chiral resolution processes, which severely hinder their development. In this work, we report a chiral tether-guided synthesis strategy. By introducing a strained planar chiral alkyl chain tether into the fused-ring building unit of the nanoring, the energy differences between the various atropisomers of the nanoring are significantly increased. This guides the formation of the thermodynamically most stable <i>D</i> <sub><i>n</i></sub> -symmetric isomer during synthesis, thus greatly enhancing the selectivity. Four chiral nanorings, <i>D</i> <sub>3</sub>-(<i>P</i>)-NR1, <i>D</i> <sub>4</sub>-(<i>P</i>)-NR1, <i>D</i> <sub>3</sub>-(<i>M</i>)-NR2, and <i>D</i> <sub>4</sub>-(<i>M</i>)-NR2, as well as their enantiomers, were facilely obtained through this method. All molecules have shown remarkable and stable CPL capability, with a luminescence dissymmetry factor up to 0.076.

Authors

Institutions

Publication Details

Journal
Chemical Science
Published
2025-01-01
DOI
https://doi.org/10.1039/d5sc06445g
Citations
1
Primary Topic
Supramolecular Self-Assembly in Materials
Type
article
Field-Weighted Citation Impact
0.60

Funders

Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Chiral tether-guided selective synthesis of D n -symmetric chiral conjugated nanorings

Yuanpeng Xie, Tao An, Jiayao Yao, Liming Ding et al.
1 citations
Chemical Science
Supramolecular Self-Assembly in Materials
0.60
article

Chiral tether-guided selective synthesis of D n -symmetric chiral conjugated nanorings

Yuanpeng Xie, Tao An, Jiayao Yao, Liming Ding, Chuantian Zuo, Yueyue Gao, Zhiyu Huang, Junqiao Ding, Yu Qi, Xinyue Zhang, Yu Wang, Yixiao Song, Zhen Xiao, Menglan Lv, Zheng Ding
article en
1 citations

Abstract

Chiral conjugated nanorings with <i>D</i> <sub><i>n</i></sub> symmetry exhibit extraordinary circularly polarized luminescence (CPL) properties due to their unique cylindrical helical conjugated system. However, their synthesis faces challenges such as numerous atropisomers and tedious separation and chiral resolution processes, which severely hinder their development. In this work, we report a chiral tether-guided synthesis strategy. By introducing a strained planar chiral alkyl chain tether into the fused-ring building unit of the nanoring, the energy differences between the various atropisomers of the nanoring are significantly increased. This guides the formation of the thermodynamically most stable <i>D</i> <sub><i>n</i></sub> -symmetric isomer during synthesis, thus greatly enhancing the selectivity. Four chiral nanorings, <i>D</i> <sub>3</sub>-(<i>P</i>)-NR1, <i>D</i> <sub>4</sub>-(<i>P</i>)-NR1, <i>D</i> <sub>3</sub>-(<i>M</i>)-NR2, and <i>D</i> <sub>4</sub>-(<i>M</i>)-NR2, as well as their enantiomers, were facilely obtained through this method. All molecules have shown remarkable and stable CPL capability, with a luminescence dissymmetry factor up to 0.076.

Chemical ScienceVol. 16(45)
Sinopec (China) (CN), Guangdong University of Technology (CN), Henan University (CN), Guizhou University (CN), Yunnan University (CN), Henan University of Technology (CN), Guizhou Minzu University (CN), National Center for Nanoscience and Technology (CN), University of Chinese Academy of Sciences (CN), Sinopec Research Institute of Petroleum Processing
National Natural Science Foundation of China, National Key Research and Development Program of China
Openalex Percentile: Top 28%
Supramolecular Self-Assembly in Materials
0.60
DOIOpen Access PDFOpenAlex
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.