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

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/debenzyl...

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Detalles Bibliográficos
Autores principales: Zhang, Jinlong, Zhu, Lu, Shen, Kang, Yang, Huameng, Hang, Xiao-Chun, Jiang, Gaoxi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6346396/
https://www.ncbi.nlm.nih.gov/pubmed/30774903
http://dx.doi.org/10.1039/c8sc03837f
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author Zhang, Jinlong
Zhu, Lu
Shen, Kang
Yang, Huameng
Hang, Xiao-Chun
Jiang, Gaoxi
author_facet Zhang, Jinlong
Zhu, Lu
Shen, Kang
Yang, Huameng
Hang, Xiao-Chun
Jiang, Gaoxi
author_sort Zhang, Jinlong
collection PubMed
description 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.
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spelling pubmed-63463962019-02-15 Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-conjugated naphthopyrans with aggregation-induced emission characters Zhang, Jinlong Zhu, Lu Shen, Kang Yang, Huameng Hang, Xiao-Chun Jiang, Gaoxi Chem Sci Chemistry 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. Royal Society of Chemistry 2018-11-02 /pmc/articles/PMC6346396/ /pubmed/30774903 http://dx.doi.org/10.1039/c8sc03837f Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Zhang, Jinlong
Zhu, Lu
Shen, Kang
Yang, Huameng
Hang, Xiao-Chun
Jiang, Gaoxi
Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-conjugated naphthopyrans with aggregation-induced emission characters
title Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-conjugated naphthopyrans with aggregation-induced emission characters
title_full Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-conjugated naphthopyrans with aggregation-induced emission characters
title_fullStr Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-conjugated naphthopyrans with aggregation-induced emission characters
title_full_unstemmed Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-conjugated naphthopyrans with aggregation-induced emission characters
title_short Brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-conjugated naphthopyrans with aggregation-induced emission characters
title_sort brønsted acid-catalyzed aromatic annulation of alkoxyallenes with naphthols: a reaction sequence to larger π-conjugated naphthopyrans with aggregation-induced emission characters
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6346396/
https://www.ncbi.nlm.nih.gov/pubmed/30774903
http://dx.doi.org/10.1039/c8sc03837f
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