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
AU - Jang, Kyungkuk
AU - Kim, Jinhwang
AU - Lee, Jeeyeon
AU - Kim, Ikyon
N1 - Publisher Copyright:
© Copyright 2019 American Chemical Society.
PY - 2019/5/13
Y1 - 2019/5/13
N2 - 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.
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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U2 - 10.1021/acscombsci.9b00006
DO - 10.1021/acscombsci.9b00006
M3 - Article
C2 - 30925043
AN - SCOPUS:85064846797
VL - 21
SP - 408
EP - 416
JO - Journal of Combinatorial Chemistry
JF - Journal of Combinatorial Chemistry
SN - 2156-8952
IS - 5
ER -