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A General Strategy to Enhance Donor‐Acceptor Molecules Using Solvent‐Excluding Substituents
Author(s) -
Hoelzel Conner A.,
Hu Hang,
Wolstenholme Charles H.,
Karim Basel A.,
Munson Kyle T.,
Jung Kwan Ho,
Zhang Han,
Liu Yu,
Yennawar Hemant P.,
Asbury John B.,
Li Xiaosong,
Zhang Xin
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201915744
Subject(s) - substituent , photochemistry , solvent , chemistry , solvent polarity , molecule , acceptor , quenching (fluorescence) , polarity (international relations) , excited state , solvent effects , polar , fluorescence , combinatorial chemistry , organic chemistry , biochemistry , physics , quantum mechanics , nuclear physics , cell , condensed matter physics , astronomy
While organic donor‐acceptor (D‐A) molecules are widely employed in multiple areas, the application of more D‐A molecules could be limited because of an inherent polarity sensitivity that inhibits photochemical processes. Presented here is a facile chemical modification to attenuate solvent‐dependent mechanisms of excited‐state quenching through addition of a β‐carbonyl‐based polar substituent. The results reveal a mechanism wherein the β‐carbonyl substituent creates a structural buffer between the donor and the surrounding solvent. Through computational and experimental analyses, it is demonstrated that the β‐carbonyl simultaneously attenuates two distinct solvent‐dependent quenching mechanisms. Using the β‐carbonyl substituent, improvements in the photophysical properties of commonly used D‐A fluorophores and their enhanced performance in biological imaging are shown.