Optical and Fluorescent Dual Sensing of Aminoalcohols by in Situ Generation of BODIPY-like Chromophore

Mukesh Eknath Shirbhate; Seongyeon Kwon; Ayoung Song; Seungha Kim; Dayeh Kim; Haofei Huang; Youngmee Kim; Hanna Lee; Sung Jin Kim; Mu Hyun Baik; Juyoung Yoon; Kwan Mook Kim

doi:10.1021/jacs.9b13232

Optical and Fluorescent Dual Sensing of Aminoalcohols by in Situ Generation of BODIPY-like Chromophore

Mukesh Eknath Shirbhate, Seongyeon Kwon, Ayoung Song, Seungha Kim, Dayeh Kim, Haofei Huang, Youngmee Kim, Hanna Lee, Sung Jin Kim, Mu Hyun Baik, Juyoung Yoon, Kwan Mook Kim

Chemistry & Nanoscience

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

18 Scopus citations

Abstract

A novel multifunctional aminophenylboronic acid connected to a diphenylketone gives both circular dichroism and fluorescence signals by in situ generation of a BODIPY-like chromophore in the presence of aminoalcohols. DFT calculations were used to understand the role of each functional group in the mechanism. This new sensor can distinguish different aminoalcohols and quantitatively indicate the concentration of the substrate, allowing for the convenient determination of the ee of racemic mixtures with a single probe. ©

Original language	English
Journal	ACS Applied Materials and Interfaces
DOIs	https://doi.org/10.1021/jacs.9b13232
State	Accepted/In press - 2020

Bibliographical note

Funding Information:
This work was supported by the grant from the National Creative Research Initiative programs of the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (No. 2012R1A3A2048814) and by the grant from NRF funded by MSIP (No. NRF-2017R1A2B2009672). We thank the Institute for Basic Science in Korea for financial support (IBS-R10-A1). Haofei Huang acknowledges the National Natural Science Foundation of China (21306107) and Natural Science Foundation of Shandong Province, China (ZR2019MB038).

Publisher Copyright:
Copyright © 2020 American Chemical Society.

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title = "Optical and Fluorescent Dual Sensing of Aminoalcohols by in Situ Generation of BODIPY-like Chromophore",

abstract = "A novel multifunctional aminophenylboronic acid connected to a diphenylketone gives both circular dichroism and fluorescence signals by in situ generation of a BODIPY-like chromophore in the presence of aminoalcohols. DFT calculations were used to understand the role of each functional group in the mechanism. This new sensor can distinguish different aminoalcohols and quantitatively indicate the concentration of the substrate, allowing for the convenient determination of the ee of racemic mixtures with a single probe. {\textcopyright}",

author = "Shirbhate, {Mukesh Eknath} and Seongyeon Kwon and Ayoung Song and Seungha Kim and Dayeh Kim and Haofei Huang and Youngmee Kim and Hanna Lee and Kim, {Sung Jin} and Baik, {Mu Hyun} and Juyoung Yoon and Kim, {Kwan Mook}",

note = "Funding Information: This work was supported by the grant from the National Creative Research Initiative programs of the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (No. 2012R1A3A2048814) and by the grant from NRF funded by MSIP (No. NRF-2017R1A2B2009672). We thank the Institute for Basic Science in Korea for financial support (IBS-R10-A1). Haofei Huang acknowledges the National Natural Science Foundation of China (21306107) and Natural Science Foundation of Shandong Province, China (ZR2019MB038). Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

doi = "10.1021/jacs.9b13232",

language = "English",

journal = "ACS Applied Materials and Interfaces",

issn = "1944-8244",

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T1 - Optical and Fluorescent Dual Sensing of Aminoalcohols by in Situ Generation of BODIPY-like Chromophore

AU - Shirbhate, Mukesh Eknath

AU - Kwon, Seongyeon

AU - Song, Ayoung

AU - Kim, Seungha

AU - Kim, Dayeh

AU - Huang, Haofei

AU - Kim, Youngmee

AU - Lee, Hanna

AU - Kim, Sung Jin

AU - Baik, Mu Hyun

AU - Yoon, Juyoung

AU - Kim, Kwan Mook

N1 - Funding Information: This work was supported by the grant from the National Creative Research Initiative programs of the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (No. 2012R1A3A2048814) and by the grant from NRF funded by MSIP (No. NRF-2017R1A2B2009672). We thank the Institute for Basic Science in Korea for financial support (IBS-R10-A1). Haofei Huang acknowledges the National Natural Science Foundation of China (21306107) and Natural Science Foundation of Shandong Province, China (ZR2019MB038). Publisher Copyright: Copyright © 2020 American Chemical Society.

PY - 2020

Y1 - 2020

N2 - A novel multifunctional aminophenylboronic acid connected to a diphenylketone gives both circular dichroism and fluorescence signals by in situ generation of a BODIPY-like chromophore in the presence of aminoalcohols. DFT calculations were used to understand the role of each functional group in the mechanism. This new sensor can distinguish different aminoalcohols and quantitatively indicate the concentration of the substrate, allowing for the convenient determination of the ee of racemic mixtures with a single probe. ©

AB - A novel multifunctional aminophenylboronic acid connected to a diphenylketone gives both circular dichroism and fluorescence signals by in situ generation of a BODIPY-like chromophore in the presence of aminoalcohols. DFT calculations were used to understand the role of each functional group in the mechanism. This new sensor can distinguish different aminoalcohols and quantitatively indicate the concentration of the substrate, allowing for the convenient determination of the ee of racemic mixtures with a single probe. ©

UR - http://www.scopus.com/inward/record.url?scp=85081681803&partnerID=8YFLogxK

U2 - 10.1021/jacs.9b13232

DO - 10.1021/jacs.9b13232

M3 - Article

C2 - 32115945

AN - SCOPUS:85081681803

SN - 1944-8244

JO - ACS Applied Materials and Interfaces

JF - ACS Applied Materials and Interfaces

ER -

Optical and Fluorescent Dual Sensing of Aminoalcohols by in Situ Generation of BODIPY-like Chromophore

Abstract

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