Synthesis and post-functionalization of alternate-linked-meta-para-[2ⁿ.1ⁿ]thiacyclophanes

Abstract

In recent decades, considerable research attention has been devoted to new synthetic procedures for thiacyclophanes. Thiacyclophanes are widely used as host molecules for the molecular recognition of organic compounds as well as metals. Herein, we report the selective and high-yielding synthesis of novel alternate-linked-meta-para-thiacyclophanes. These novel thiacyclophanes are selectively synthesized in high-yielding procedures. Furthermore, post-functionalization of the phenolic moieties was successfully performed. The 3D structure of the alternate-linked-meta-para-[22.12]thiacyclophane was further elucidated via X-ray crystallographic analysis.

Synthesis of Donor‐Acceptor π‐Conjugated Macrocycles by Post‐Functionalization†

“…Post‐functionalization on the existing macrocyclic skeleton is an effective way for the development of novel macrocycles with specific functions. [ 20‐22 ] For instance, porphyrins have been modified via multiple strategies, including cycloaddition reactions, [ 23 ] aromatic substitution reactions [ 24 ] and pyrrole ring‐contraction [ 25 ] or ‐expansion reactions [ 26 ] to render porphyrins derivatives, making them as versatile materials for the application in electronic devices, sensors and catalysis. [ 20 ] It is a mighty strategy for regulating optoelectronic properties of linear π‐conjugated oligomers and polymers by introducing donor and acceptor (D‐A) modules into their molecular skeleton.…”