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3124021 
Journal Article 
Nitropyrene Photoprobes: Making Them, and What Are They Good for? 
Espinoza, E; Xia, B; Darabedian, N; Larsen, JM; Nunez, V; Bao, D; Mac, JT; Botero, F; Wurch, M; Zhou, F; Vullev, VI 
2016 
Yes 
European Journal of Organic Chemistry
ISSN: 1434-193X
EISSN: 1099-0690 
Wiley-VCH Verlag 
2016 
2 
343-356 
English 
WOS:000368814900017 
Pyrene derivatives are among the most widely used organic fluorescent photoprobes. Many of them are photosensitizers for hole injection. Pyrenes, however, are mostly UV absorbers, limiting their utility for photonic applications. Nitration of pyrene shifts its absorption to the visible region. Conversely, nitration of pyrene that is already derivatized for covalent labeling, produces mixtures of isomers that are challenging to separate. We present a robust procedure for attaining isomerically pure nitropyrenes. NMR analysis provides unequivocal assignments of the regioisomers and of the structures of the disubstituted nitropyrenes. The added substituents negligibly affect the electronic properties of the nitropyrenes. Photoexcited nitropyrenes undergo efficient triplet formation, making them an attractive choice for triplet sensitizers and photooxidants. Hence, facile and reliable preparation of disubstituted nitropyrenes provides venues for exploring their electronic and photonic utility. Copyright © 2016 Wiley-VCH Verlag GmbH & Co. KGaA. 
Sensitizers; Triplet sensitizer; Fluorecent probes; Electron acceptor; Nitration; Conformational dynamics