Design and spectroscopic characterization of novel series of near infrared indocyanine dyes

• Published in: Journal of molecular structure 2015-07, Vol.1091, p.228-235
• Main Authors: Abd-El-Aziz, Alaa S., Strohm, Elizabeth A., Okasha, Rawda M.
• Format: Article
• Language: English
• Subjects: H-aggregation; Heptamethine indocyanine dyes; Near infrared dyes
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2015.02.037

[Display omitted] •A new series of near infrared heptamethine indocyanine dyes have been synthesized.•The structures of the new dyes have been determined.•The ester substituents control molar absorptivity and fluorescence quantum yields.•H-aggregate formation of the new dyes was investigated. A novel series of near infrared heptamethine indocyanine dyes bearing various aromatic chromophores has been synthesized. The synthetic methodology was achieved via ester condensation reactions of heptamethine indocyanine parent dye with carboxylic moiety and aromatic compounds such as anthracene, pyrene and thiophene derivatives. Structural analysis of the newly prepared dyes was accomplished using one- and two-dimensional nuclear magnetic resonance, infrared spectroscopy and electrospray ionization mass spectrometry. These dyes exhibited high molar absorptivity based on the UV–visible/near-infrared spectral data. Fluorescence emission spectral data was used to determine the relative quantum yield. The new dyes displayed formation of H-aggregates in water at low concentrations, while this behavior was not observed in methanol.