Intramolecular Electrophilic Cyclization Approach to 6-Substituted Naphtho[2,1- b]benzofurans: Novel Dual-State Emissive Fluorophores with Blue Emission

Dileep Kumar Singh; Kyungkuk Jang; Jinhwang Kim; Jeeyeon Lee; Ikyon Kim

doi:10.1021/acscombsci.9b00006

Intramolecular Electrophilic Cyclization Approach to 6-Substituted Naphtho[2,1- b]benzofurans: Novel Dual-State Emissive Fluorophores with Blue Emission

Dileep Kumar Singh, Kyungkuk Jang, Jinhwang Kim, Jeeyeon Lee, Ikyon Kim

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

A regiospecific synthesis of naphtho[2,1-b]benzofurans with a substituent at the C6 position was achieved via intramolecular 6-endo-dig electrophilic cyclization under acidic conditions to construct the central aromatic C ring. Screening of the synthesized compounds using a high-content imaging system enabled us to discover novel dual state emissive compounds 2{1,6}, 2{1,8}, and 2{4,3}, which are highly emissive with blue emission in their solid states as well as in solution states in most solvents. In addition, the compounds 2{4,3}, 2{4,12}, and 2{5,13} were found to be the most cell permeable in HeLa cells for live cell imaging with negligible phototoxicity.

Original language	English
Pages (from-to)	408-416
Number of pages	9
Journal	ACS Combinatorial Science
Volume	21
Issue number	5
DOIs	https://doi.org/10.1021/acscombsci.9b00006
Publication status	Published - 2019 May 13

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© Copyright 2019 American Chemical Society.

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1021/acscombsci.9b00006

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title = "Intramolecular Electrophilic Cyclization Approach to 6-Substituted Naphtho[2,1- b]benzofurans: Novel Dual-State Emissive Fluorophores with Blue Emission",

abstract = "A regiospecific synthesis of naphtho[2,1-b]benzofurans with a substituent at the C6 position was achieved via intramolecular 6-endo-dig electrophilic cyclization under acidic conditions to construct the central aromatic C ring. Screening of the synthesized compounds using a high-content imaging system enabled us to discover novel dual state emissive compounds 2{1,6}, 2{1,8}, and 2{4,3}, which are highly emissive with blue emission in their solid states as well as in solution states in most solvents. In addition, the compounds 2{4,3}, 2{4,12}, and 2{5,13} were found to be the most cell permeable in HeLa cells for live cell imaging with negligible phototoxicity.",

author = "Singh, {Dileep Kumar} and Kyungkuk Jang and Jinhwang Kim and Jeeyeon Lee and Ikyon Kim",

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doi = "10.1021/acscombsci.9b00006",

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journal = "ACS Combinatorial Science",

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Intramolecular Electrophilic Cyclization Approach to 6-Substituted Naphtho[2,1- b]benzofurans : Novel Dual-State Emissive Fluorophores with Blue Emission. / Singh, Dileep Kumar; Jang, Kyungkuk; Kim, Jinhwang; Lee, Jeeyeon; Kim, Ikyon.

In: ACS Combinatorial Science, Vol. 21, No. 5, 13.05.2019, p. 408-416.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Intramolecular Electrophilic Cyclization Approach to 6-Substituted Naphtho[2,1- b]benzofurans

T2 - Novel Dual-State Emissive Fluorophores with Blue Emission

AU - Singh, Dileep Kumar

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AU - Kim, Jinhwang

AU - Lee, Jeeyeon

AU - Kim, Ikyon

PY - 2019/5/13

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AB - A regiospecific synthesis of naphtho[2,1-b]benzofurans with a substituent at the C6 position was achieved via intramolecular 6-endo-dig electrophilic cyclization under acidic conditions to construct the central aromatic C ring. Screening of the synthesized compounds using a high-content imaging system enabled us to discover novel dual state emissive compounds 2{1,6}, 2{1,8}, and 2{4,3}, which are highly emissive with blue emission in their solid states as well as in solution states in most solvents. In addition, the compounds 2{4,3}, 2{4,12}, and 2{5,13} were found to be the most cell permeable in HeLa cells for live cell imaging with negligible phototoxicity.

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Intramolecular Electrophilic Cyclization Approach to 6-Substituted Naphtho[2,1- b]benzofurans: Novel Dual-State Emissive Fluorophores with Blue Emission

Abstract

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