Citation: Yue Li, Qianyu Ding, Wansheng Liu, Yimeng Sun, Liyao Liu, Ye Zou, Yutao Cui, Jia Zhu, Chongan Di, Daoben Zhu. Bipyridine-bridged Φ-shaped cyclo[8]thiophene[2]pyrrole: Synthesis and fluorescence properties[J]. Chinese Chemical Letters, ;2026, 37(2): 111989. doi: 10.1016/j.cclet.2025.111989 shu

Bipyridine-bridged Φ-shaped cyclo[8]thiophene[2]pyrrole: Synthesis and fluorescence properties

Yue Li ^{a, 1} ,
Qianyu Ding ^{b, c, 1} ,
Wansheng Liu ^a ,
Yimeng Sun ^{a, *,} ,
Liyao Liu ^a ,
Ye Zou ^a ,
Yutao Cui ^{a, *,} ,
Jia Zhu ^{b, c, *,} ,
Chongan Di ^a ,
Daoben Zhu ^{a, c}

a.
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry Chinese Academy of Sciences, Beijing 100190, China
b.
Laboratory of Theoretical and Computational Nanoscience, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Chinese Academy of Sciences, Beijing 100190, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

sunyimeng@iccas.ac.cn

ytcui@iccas.ac.cn

zhujia@nanoctr.cn

Received Date: 24 June 2025
Revised Date: 16 October 2025
Accepted Date: 20 October 2025
Available Online: 21 October 2025

Figures(5)

Cyclo[n]Thiophenes (CnTs) are a distinctive class of π-conjugated macrocyclic molecules that have attracted growing attention owing to their structural aesthetics and organic electronic characteristics. However, the development of CnTs has been largely impeded by inefficient synthetic route. In this work, we employ a bridge strategy using bipyridine as bridge to link two quaterthiophene units resulting in Φ-shaped bicyclosystem. This strain-retaining approach improves the synthesis efficiency of the macrocycles. Two new macrocyclic molecules, (4T-2hexyl-2Me)₂-DPBP and (4T-2hexyl)₂-DPBP, were successfully synthesized in total yield 17% and 16%, respectively. Single-crystal structure of (4T-2hexyl-2Me)₂-DPBP reveals that the bipyridine bridge is orthogonally strapped by two quaterthiophene units. Notably, both compounds exhibit aggregation-induced emission enhancement (AIEE) behavior-an unprecedented feature among CnT-based macrocycles. Theoretical calculations reveal that this AIE phenomenon originates from the restriction of intramolecular motion (RIM) in the aggregated state, which suppresses the non-radiative decay channels. These results demonstrate a generalized strategy for the synthesis of functional π-conjugated macrocyclic molecules based fluorescent materials.
- Macrocycles,
- Oligothiophenes,
- CnTs,
- Fluorescence,
- AIEE
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