A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes
Publication type: Journal Article
Publication date: 2021-01-21
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
33245605
General Chemistry
Catalysis
Abstract
Installation of a carbanionic substituent, that is strongly stabilised by two (trifluoromethyl)sulfonyl (Tf = SO 2 CF 3 ) groups, into several fluorescence dyes including boron-dipyrromethenes (BODIPYs), fluoresceins, and aminocoumarins has been achieved by the 2,2-bis(triflyl)ethylation reaction of the dye frameworks with highly electrophilic Tf 2 C=CH 2 , followed by neutralisation with NaHCO 3 . Despite the contradiction between water-solubility and lipophilicity, the carbanion-decorated dyes thus obtained showed significant enhancement of not only water-solubility but also lipophilicity. This work clearly demonstrates that the fluorinated, highly stabilised carbanionic substituent is a new option for controlling the macroscopic property of chemical materials.
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Total citations:
40
Citations from 2024:
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(35%)
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Yanai H. et al. A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes // Angewandte Chemie - International Edition. 2021. Vol. 60. No. 10. pp. 5168-5172.
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Yanai H., Hoshikawa S., Moriiwa Y., Shoji A., Yanagida A., MATSUMOTO T. A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes // Angewandte Chemie - International Edition. 2021. Vol. 60. No. 10. pp. 5168-5172.
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TY - JOUR
DO - 10.1002/anie.202012764
UR - https://doi.org/10.1002/anie.202012764
TI - A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes
T2 - Angewandte Chemie - International Edition
AU - Yanai, Hikaru
AU - Hoshikawa, Shoki
AU - Moriiwa, Yukiko
AU - Shoji, Atsushi
AU - Yanagida, Akio
AU - MATSUMOTO, TAKASHI
PY - 2021
DA - 2021/01/21
PB - Wiley
SP - 5168-5172
IS - 10
VL - 60
PMID - 33245605
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex (up to 50 authors)
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@article{2021_Yanai,
author = {Hikaru Yanai and Shoki Hoshikawa and Yukiko Moriiwa and Atsushi Shoji and Akio Yanagida and TAKASHI MATSUMOTO},
title = {A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes},
journal = {Angewandte Chemie - International Edition},
year = {2021},
volume = {60},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/anie.202012764},
number = {10},
pages = {5168--5172},
doi = {10.1002/anie.202012764}
}
Cite this
MLA
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Yanai, Hikaru, et al. “A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes.” Angewandte Chemie - International Edition, vol. 60, no. 10, Jan. 2021, pp. 5168-5172. https://doi.org/10.1002/anie.202012764.