Premium
Nitropyrene Photoprobes: Making Them, and What Are They Good for?
Author(s) -
Espinoza Eli M.,
Xia Bing,
Darabedian Narek,
Larsen Jillian M.,
Nuñez Vicente,
Bao Duoduo,
Mac Jenny T.,
Botero Fabian,
Wurch Michelle,
Zhou Feimeng,
Vullev Valentine I.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501339
Subject(s) - chemistry , pyrene , nitration , structural isomer , limiting , absorption (acoustics) , covalent bond , fluorescence , photochemistry , combinatorial chemistry , computational chemistry , organic chemistry , mechanical engineering , quantum mechanics , engineering , physics , acoustics
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.