@article{62710bc83c0e4fb9b50bc68d15994dcf,
title = "A General Strategy to Enhance Donor-Acceptor Molecules Using Solvent-Excluding Substituents",
abstract = "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.",
author = "Hoelzel, {Conner A.} and Hang Hu and Wolstenholme, {Charles H.} and Karim, {Basel A.} and Munson, {Kyle T.} and Jung, {Kwan Ho} and Han Zhang and Yu Liu and Yennawar, {Hemant P.} and Asbury, {John B.} and Xiaosong Li and Xin Zhang",
note = "Funding Information: We thank A. Winter, R. Giri, and S. Benkovic for their contributed insight and helpful discussions as well as J. Cotruvo for access to his UV/Vis instrumentation. We thank the Burroughs Wellcome Fund Career Award at the Scientific Interface (X.Z.), Paul Berg Early Career Professorship (X.Z.), Lloyd and Dottie Huck Early Career Award (X.Z.), Sloan Research Fellowship (X.Z.), PEW Biomedical Scholars Program (X.Z.), and NSF CHE‐1856210 (X.L.) for support. We thank Dr. Gang Ning and Ms. Missy Hazen of the Penn State Microscopy Core Facility and Dr. Tatiana Laremore of the Penn State Proteomics and Mass Spectrometry Core Facility for technical assistance. We thank Prof. Raymond Shaak for assistance with synthetic apparatus. Funding Information: We thank A. Winter, R. Giri, and S. Benkovic for their contributed insight and helpful discussions as well as J. Cotruvo for access to his UV/Vis instrumentation. We thank the Burroughs Wellcome Fund Career Award at the Scientific Interface (X.Z.), Paul Berg Early Career Professorship (X.Z.), Lloyd and Dottie Huck Early Career Award (X.Z.), Sloan Research Fellowship (X.Z.), PEW Biomedical Scholars Program (X.Z.), and NSF CHE-1856210 (X.L.) for support. We thank Dr. Gang Ning and Ms. Missy Hazen of the Penn State Microscopy Core Facility and Dr. Tatiana Laremore of the Penn State Proteomics and Mass Spectrometry Core Facility for technical assistance. We thank Prof. Raymond Shaak for assistance with synthetic apparatus. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2020",
month = mar,
day = "16",
doi = "10.1002/anie.201915744",
language = "English (US)",
volume = "59",
pages = "4785--4792",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "12",
}