Imaging Science and Photochemistry ›› 2012, Vol. ›› Issue (5): 375-383.DOI: 10.7517/j.issn.1674-0475.2012.05.375

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Synthesis, Characterization and Spectral Properties of Novel Meso-Substituted Heptamethine Cyanine Dye

CHEN Xiu-ying, GUO Lin, JIA Xian-lin, GAO Hai-yan, ZHENG Chang-ge   

  1. The Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu, P. R. China
  • Received:2012-04-19 Revised:2012-05-15 Online:2012-09-15 Published:2012-05-25

Abstract: Two novel meso-substituted heptamethine cyanine dyes were prepared and characterized by 1HNMR and HRMS spectra. The absorption and emission spectral properties in different solvents were studied. The maxima of the absorption and fluorescent spectra of the dyes 3b and 3c were at 677/790 nm and 647/786 nm in methanol respectively with larger stokes shifts of 113 nm and 139 nm. The photo-degradation reaction showed that the rate constants for the three dyes 3a-3c were 1.21?10-3 mol/min, 1.81?10-3 mol/min and 2.14?10-3 mol/min respectively. Cyclic voltammetry showed that the oxidative potentials for 3a-3c were 0.729 V, 0.624 V and 0.598 V respectively. The experiment of photodegradation showed that electron-withdrawing group on methine chain of heptamethine cyanine dye enhanced the photostability and electron-donating group on methine chain decreased the photostability of the dyes. The ability of donating and withdrawing affected the photostability of the dyes. The hydrogen bond on substituted atom on methine chain was favor for enhancing the photostability of the dyes. And hydrogen bond of chlorine atom on methine chain was in favor of enhancing the photostability of the dyes. But nitrogen atom on methine chain can not form hydrogen bond and not helpful for the photostability of the dyes.

Key words: heptamethine cyanine dye, near-infrared, absorption spectra, fluorescent spectra, photostability, synthesis, label

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