Long-wavelength analogue of PRODAN: Synthesis and properties of Anthradan, a fluorophore with a 2,6-donor-acceptor anthracene structure
Long-wavelength analogue of PRODAN: Synthesis and properties of Anthradan, a fluorophore with a 2,6-donor-acceptor anthracene structure
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DOI：
10.1021/jo0616660
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发表时间：
2006-12-22
影响因子：
3.6
通讯作者：
Twieg, Robert J.
中科院分区：
文献类型：
--
作者：
Lu, Zhikuan;Lord, Samuel J.;Twieg, Robert J.
我们以2,6-二氨基蒽醌为原料，合成了环境敏感荧光团2-氰基-6-二己氨基蒽和2-丙酰基-6-二己氨基蒽（Anthradan）。 Anthradan 是著名的萘 2-丙酰基-6-二甲氨基萘 (PRODAN) 荧光团家族的苯系物。蒽额外的光谱红移避免了许多生物系统的自发荧光，并为荧光应用提供了更有利的激发波长。此外，Anthradan 表现出与 PRODAN 相当的极性敏感发射，并在多种溶剂中表现出高量子产率。这些含蒽荧光团的单分子已在聚合物主体中成像作为原理证明。
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.