Issue 4, 2019

Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-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 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

Supplementary files

Article information

Article type
Edge Article
Submitted
28 Aug 2018
Accepted
01 Nov 2018
First published
02 Nov 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 1070-1074

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, 10, 1070 DOI: 10.1039/C8SC03837F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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