Synthesis of macrocyclic bis(phenylbenzoxazole) derivatives via tandem claisen rearrangement and their fluorescence behavior

✍ Scribed by Emiko Koyama; Hideo Tokuhisa; Yoshinobu Nagawa; Gang Yang; Kazuhisa Hiratani

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2001
• Tongue: English
• Weight: 102 KB
• Volume: 38
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570380617

✦ Synopsis

Abstract

Novel macrocyclic bis(phenylbenzoxazole) derivatives were easily synthesized from macrocyclic isobutenyl bis(amide‐ether)s by tandem Claisen rearrangement and subsequent intramolecular cyclization of the amide‐phenol intermediates. The position of substitution of the oligoethylene glycol moiety on the phenylamido groups of the macrocycles did not have a large effect on the yields of the bis(benzoxazole)s for the meta and para derivatives. The fluorescence quantum yields of most of the macrocyclic bis(benzoxa‐zole)s were lower than those of the corresponding nonmacrocyclic bis(benzoxazole) model compounds. The quantum yields of the para‐substituted macrocyclic bis(benzoxazole)s were clearly lower than those of the model compounds and decreased with increasing length of the oligoethylene chain.