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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

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Abstract

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.

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

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Publication details

The article was received on 28 Aug 2018, accepted on 01 Nov 2018 and first published on 02 Nov 2018


Article type: Edge Article
DOI: 10.1039/C8SC03837F
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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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

    J. Zhang, L. Zhu, K. Shen, H. Yang, X. Hang and G. Jiang, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC03837F

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