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Title: Substantial Intramolecular Charge Transfer Induces Long Emission Wavelengths and Mega Stokes Shifts in 6-Aminocoumarins

Abstract

Coumarins are deployed in numerous bioimaging and biosensing applications. Among various coumarin derivatives, 6-aminocoumarins attract increasing attention for their red-shifted emissions, mega Stokes shifts, and significant solvatochromism. These spectral characteristics together with weak emission intensities have historically been ascribed to the formation of the twisted intramolecular charge transfer (TICT) state in 6-aminocoumarins. In this work, we demonstrate that it is actually substantial intramolecular charge transfer (ICT) that is responsible for these fluorescent properties. Based on this new understanding, we reanalyzed the sensing mechanism of a 6-aminocouarmin based fluorescent probe and obtained close agreement with experimental data. Lastly, our results lead to a deeper understanding of the photophysics of 6-aminocoumarins and will inspire the rational development of novel fluorescent probes.

Authors:
ORCiD logo [1]; ORCiD logo [2];  [3]
  1. Univ. of Cambridge, Cambridge (United Kingdom); Singapore Univ. of Technology and Design (Singapore); Singapore-MIT Alliance for Research and Technology (SMART) (Singapore)
  2. Univ. of Cambridge, Cambridge (United Kingdom); STFC Rutherford Appleton Lab., Didcot (United Kingdom); Argonne National Lab. (ANL), Argonne, IL (United States)
  3. Chinese Academy of Sciences, Dalian (China)
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1376720
Grant/Contract Number:  
AC02-06CH11357
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Journal of Physical Chemistry. C
Additional Journal Information:
Journal Volume: 121; Journal Issue: 24; Journal ID: ISSN 1932-7447
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Liu, Xiaogang, Cole, Jacqueline M., and Xu, Zhaochao. Substantial Intramolecular Charge Transfer Induces Long Emission Wavelengths and Mega Stokes Shifts in 6-Aminocoumarins. United States: N. p., 2017. Web. doi:10.1021/acs.jpcc.7b04176.
Liu, Xiaogang, Cole, Jacqueline M., & Xu, Zhaochao. Substantial Intramolecular Charge Transfer Induces Long Emission Wavelengths and Mega Stokes Shifts in 6-Aminocoumarins. United States. doi:10.1021/acs.jpcc.7b04176.
Liu, Xiaogang, Cole, Jacqueline M., and Xu, Zhaochao. Thu . "Substantial Intramolecular Charge Transfer Induces Long Emission Wavelengths and Mega Stokes Shifts in 6-Aminocoumarins". United States. doi:10.1021/acs.jpcc.7b04176. https://www.osti.gov/servlets/purl/1376720.
@article{osti_1376720,
title = {Substantial Intramolecular Charge Transfer Induces Long Emission Wavelengths and Mega Stokes Shifts in 6-Aminocoumarins},
author = {Liu, Xiaogang and Cole, Jacqueline M. and Xu, Zhaochao},
abstractNote = {Coumarins are deployed in numerous bioimaging and biosensing applications. Among various coumarin derivatives, 6-aminocoumarins attract increasing attention for their red-shifted emissions, mega Stokes shifts, and significant solvatochromism. These spectral characteristics together with weak emission intensities have historically been ascribed to the formation of the twisted intramolecular charge transfer (TICT) state in 6-aminocoumarins. In this work, we demonstrate that it is actually substantial intramolecular charge transfer (ICT) that is responsible for these fluorescent properties. Based on this new understanding, we reanalyzed the sensing mechanism of a 6-aminocouarmin based fluorescent probe and obtained close agreement with experimental data. Lastly, our results lead to a deeper understanding of the photophysics of 6-aminocoumarins and will inspire the rational development of novel fluorescent probes.},
doi = {10.1021/acs.jpcc.7b04176},
journal = {Journal of Physical Chemistry. C},
number = 24,
volume = 121,
place = {United States},
year = {Thu Jun 01 00:00:00 EDT 2017},
month = {Thu Jun 01 00:00:00 EDT 2017}
}

Journal Article:
Free Publicly Available Full Text
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Cited by: 10 works
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