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- Title
Evaluation of Anisole-Substituted Boron Difluoride Formazanate Complexes for Fluorescence Cell Imaging.
- Authors
Maar, Ryan R.; Barbon, Stephanie M.; Sharma, Neha; Groom, Hilary; Luyt, Leonard G.; Gilroy, Joe B.
- Abstract
Evaluation of three subclasses of boron difluoride formazanate complexes bearing o-, m-, and p-anisole N-aryl substituents (Ar) as readily accessible alternatives to boron dipyrromethene (BODIPY) dyes for cell imaging applications is described. While the wavelengths of maximum absorption ( λmax) and emission ( λem) observed for each subclass of complexes, which differed by their carbon-bound substituents (R), were similar, the emission quantum yields for 7 a- c (R=cyano) were enhanced relative to 8 a- c (R=nitro) and 9 a- c (R=phenyl). Complexes 7 a- c and 8 a- c were also significantly easier to reduce electrochemically to their radical anion and dianion forms compared to 9 a- c. Within each subclass, the o-substituted derivatives were more difficult to reduce, had shorter λmax and λem, and lower emission quantum yields than the p-substituted analogues as a result of sterically driven twisting of the N-aryl substituents and a decrease in the degree of π-conjugation. The m-substituted complexes were the least difficult to reduce and possessed intermediate λmax, λem, and quantum yields. The complexes studied also exhibited large Stokes shifts (82-152 nm, 2143-5483 cm−1). Finally, the utility of complex 7 c (Ar= p-anisole, R=cyano), which can be prepared for just a few dollars per gram, for fluorescence cell imaging was demonstrated. The use of 7 c and 4′,6-diamino-2-phenylindole (DAPI) allowed for simultaneous imaging of the cytoplasm and nucleus of mouse fibroblast cells.
- Subjects
BORON; ANALYTICAL chemistry; ANISOLE; CELL imaging; WAVELENGTHS; LABORATORY mice
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 44, p15589
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201502821