Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor-Acceptor Anthracene Structure

by: Z Lu, SJ Lord, H Wang, WE Moerner, RJ Twieg

J Org Chem, Vol. 71, No. 26. (Dec 2006), pp. 9651-9657.

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http://www.hubmed.org/display.cgi?uids=17…, DOI, American Chem. Soc. Publications

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Abstract

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.

@article{Lu:2006:J-Org-Chem:17168582, abstract = {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.}, author = {Lu, Z. and Lord, S. J. and Wang, H. and Moerner, W. E. and Twieg, R. J. }, citeulike-article-id = {1022603}, doi = {10.1021/jo0616660}, journal = {J Org Chem}, keywords = {fluorophores, solvatochromism}, month = {Dec}, number = {26}, pages = {9651--9657}, posted-at = {2007-01-02 23:36:40}, priority = {0}, title = {Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor-Acceptor Anthracene Structure}, url = {http://www.hubmed.org/display.cgi?uids=17168582}, volume = {71}, year = {2006} }

RIS record

TY - JOUR ID - Lu:2006:J-Org-Chem:17168582 L3 - citeulike-article-id:1022603 TI - Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor-Acceptor Anthracene Structure JF - J Org Chem VL - 71 IS - 26 SP - 9651 EP - 9657 N2 - 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. KW - fluorophores KW - solvatochromism AU - Lu, Z AU - Lord, SJ AU - Wang, H AU - Moerner, WE AU - Twieg, RJ PY - 2006/Dec// UR - http://www.hubmed.org/display.cgi?uids=17168582 ER -

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