Modification of Electron Acceptors with Fused Alicyclic Rings through Inverse Electron-Demand Diels-Alder Reactions to Tune the Optical Properties of Conjugated Polymers

Modification of Electron Acceptors with Fused Alicyclic Rings through Inverse Electron-Demand Diels-Alder Reactions to Tune the Optical Properties of Conjugated Polymers

Materials Advances

DOI 10.1039/D5MA00507H

https://doi.org/10.1039/d5ma00507h

Dinghui Chen, Kang Le Osmund Chin, Xiang Yun Debbie Soo, Fengxia Wei, Ke Li, Pin Jin Ong, Qiang Zhu, Xi Zu Wang, Teck Lip Dexter Tam, Zhuang Mao Png, Ming Hui Chua, Hong Meng, Jianwei Xu

General Materials Science

27 August 2025

Chen, D., Chin, K. L. O., Soo, X. Y. D., Wei, F., Li, K., Ong, P. J., Zhu, Q., Wang, X. Z., Tam, T. L. D., Png, Z. M., Chua, M. H., Meng, H., & Xu, J. (2025). Modification of Electron Acceptors with Fused Alicyclic Rings through Inverse Electron-Demand Diels-Alder Reactions to Tune the Optical Properties of Conjugated Polymers. Materials Advances. https://doi.org/10.1039/d5ma00507h

Traditional strategies for manipulating the optical properties of conjugated polymers primarily focus on modifications of the polymer backbone, including donor–acceptor engineering and adjusting the conjugation length. Here, we report a novel approach to modulate the electronic structure of conjugated polymers by incorporating alicyclic rings through inverse electron-demand Diels–Alder reactions. Two conjugated polymers, PCT-8 and PBT-7, were synthesized using monomers with an eight-membered and a bridged six-membered aliphatic ring, respectively. These structural modifications lead to noticeable changes in UV-visible absorption (Δλmax = 47 nm for PCT-8 and PBT-7), optical band gaps (2.38 eV and 2.19 eV, PCT-8 and PBT-7, respectively), polymer packing, and intermolecular interactions, while maintaining the integrity of the polymer backbone. Besides, both polymers demonstrate electrochromic properties. This strategy offers a versatile, minimally invasive method for tuning the optical properties of conjugated polymers, paving the way for the design of multifunctional materials for optoelectronic applications.

Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)

This research / project is supported by the Agency for Science, Technology and Research - Horizontal Technology Coordinating Offices Fund
Grant Reference no. : C231218001

https://oar.a-star.edu.sg/communities-collections/articles/22220

2633-5409

Institute of Chemical and Engineering Sciences

https://doi.org/10.1039/d5ma00507h