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Molecules 2016, 21(1), 23; doi:10.3390/molecules21010023

Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties

1
Department of Chemistry, Georgia State University, 50 Decatur St., Atlanta, GA 30303, USA
2
Center for Diagnostics and Therapeutics, Georgia State University, Petit Science Center, 100 Piedmont Ave SE, Atlanta, GA 30303, USA
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Pani Koutentis
Received: 4 September 2015 / Revised: 17 December 2015 / Accepted: 18 December 2015 / Published: 24 December 2015
View Full-Text   |   Download PDF [3922 KB, uploaded 24 December 2015]   |  

Abstract

Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form. View Full-Text
Keywords: cyanine dye; unsymmetrical; synthesis; optical properties; DFT calculations; DNA grooves cyanine dye; unsymmetrical; synthesis; optical properties; DFT calculations; DNA grooves
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Soriano, E.; Holder, C.; Levitz, A.; Henary, M. Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties. Molecules 2016, 21, 23.

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