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Bronsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger ?-conjugated naphthopyrans with aggregation-induced emission characters.

ABSTRACT: A practical and readily scalable reaction sequence was developed for the straightforward synthesis of a new family of larger ?-conjugated naphthopyrans by a Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with inert naphthols. The cascade pathway involves allylation/cyclization/debenzyloxylation/isomerization/dehydration. The new class of solid state diphenylmethylene substituted naphthopyrans are fluorescent emissive and proved to have aggregation-induced emission (AIE) behavior.

SUBMITTER: Zhang J

PROVIDER: S-EPMC6346396 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-conjugated naphthopyrans with aggregation-induced emission characters.

Zhang Jinlong J Zhu Lu L Shen Kang K Yang Huameng H Hang Xiao-Chun XC Jiang Gaoxi G

Chemical science 20181102 4

A practical and readily scalable reaction sequence was developed for the straightforward synthesis of a new family of larger π-conjugated naphthopyrans by a Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with inert naphthols. The cascade pathway involves allylation/cyclization/debenzyloxylation/isomerization/dehydration. The new class of solid state diphenylmethylene substituted naphthopyrans are fluorescent emissive and proved to have aggregation-induced emission (AIE) behavior. ...[more]

PMID: 30774903

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