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- Title
On-surface synthesis and spontaneous segregation of conjugated tetraphenylethylene macrocycles.
- Authors
Li, En; Lyu, Cheng-Kun; Chen, Chengyi; Xie, Huilin; Zhang, Jianyu; Lam, Jacky Wing Yip; Tang, Ben Zhong; Lin, Nian
- Abstract
Creating conjugated macrocycles has attracted extensive research interest because their unique chemical and physical properties, such as conformational flexibility, intrinsic inner cavities and aromaticity/antiaromaticity, make these systems appealing building blocks for functional supramolecular materials. Here, we report the synthesis of four-, six- and eight-membered tetraphenylethylene (TPE)-based macrocycles on Ag(111) via on-surface Ullmann coupling reactions. The as-synthesized macrocycles are spontaneously segregated on the surface and self-assemble as large-area two-dimensional mono-component supramolecular crystals, as characterized by scanning tunneling microscopy (STM). We propose that the synthesis benefits from the conformational flexibility of the TPE backbone in distinctive multi-step reaction pathways. This study opens up opportunities for exploring the photophysical properties of TPE-based macrocycles. On-surface synthesis is a useful tool to produce extended macrocyclic structures with atomic precision, with only one type of macrocycle typically formed through on-surface coupling reactions. Here, distinct domains of four-, six- and eight-membered tetraphenylethylene-based macrocycles are synthesized on Ag(111) as segregated large-area mono-component crystals.
- Subjects
MACROCYCLIC compounds; SCANNING tunneling microscopy; TETRAPHENYLETHYLENE; ATOMIC structure; CHEMICAL properties; ANTIAROMATICITY
- Publication
Communications Chemistry, 2022, Vol 5, Issue 1, p1
- ISSN
2399-3669
- Publication type
Article
- DOI
10.1038/s42004-022-00794-1