Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 26, Pages 9651-9657Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0616660
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Funding
- NHGRI NIH HHS [P20 HG003638, P20 HG003638-03, 5P20-HG003638-02] Funding Source: Medline
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We have synthesized the environment-sensitive fluorophores 2-cyano-6-dihexylaminoanthracene and 2-propionyl-6-dihexylaminoanthracene (Anthradan) starting from 2,6-diaminoanthraquinone. Anthradan is the benzologue of the well-known family of naphthalene 2-propionyl-6-dimethylaminonaphthalene (PRODAN) fluorophores. The additional spectral red shift of the anthracene avoids the autofluorescence of many biological systems and provides for more favorable excitation wavelengths for fluorescence applications. Furthermore, Anthradan exhibits polarity-sensitive emission comparable to that of PRODAN and displays high quantum yields in a range of solvents. Single molecules of these anthracene-containing fluorophores have been imaged in polymer hosts as a proof-of-principle.
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