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http://dx.doi.org/10.12772/TSE.2022.59.264

Synthesis and Optical Properties of Heptamethine Indolenine Cyanine Dyes Containing Various Counter Anions  

Park, Se Jeong (School of Chemical Engineering, Pusan National University)
Gopal, Balamurugan (School of Chemical Engineering, Pusan National University)
Jang, Jae Woong (School of Chemical Engineering, Pusan National University)
Park, Jong S. (School of Chemical Engineering, Pusan National University)
Publication Information
Textile Science and Engineering / v.59, no.5, 2022 , pp. 264-270 More about this Journal
Abstract
Cyanine dyes exhibit excellent spectral properties, featuring broad wavelength tunability and a high absorption coefficient. However, for optimal spectral properties, they need to retain a monomeric state, which alleviates aggregation. Herein, we present the synthesis and properties of hexyl-substituted heptamethine indolenine cyanine dye containing various anions. The prepared cyanine dye exhibited strong absorption properties at approximately 800 nm in the near-infrared region. Different counter anions, including bromide (Br), tetrafluoroborate (BF4), bis(trifluoromethanesulfonyl)imide (TFSI), and tetrakis (pentafluorophenyl)borate (TPFB), were incorporated to examine the effect on the aggregational and resulting optical behaviors. Among these, the cyanine with TPFB anions showed a preferential monomeric peak in the UV-Vis spectra, indicating that the large TPFB anion acts as a potent aggregation inhibitor. Furthermore, the photothermal performance of the cyanine dye with the TPFB anion was evaluated, exhibiting a suitable temperature profile, kinetic stability, and photothermal conversion efficiency. Furthermore, the cyanide sensing response was examined, with the prepared cyanine dyes exhibiting high binding constants and low detection limits.
Keywords
cyanine dye; counter anions; near-infrared absorption; photothermal; cyanide sensing;
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1 N.G. Medeiros, C. A. Braga, V. S. Camara, R. C. Duarte, and F. S. Rodembusch, "Near-Infrared Fluorophores Based on Heptamethine Cyanine Dyes: From Their Synthesis and Photothermal Properties to Recent Optical Sensing and Bioimaging Applications", Asian J. Org. Chem., 2022, 11, e202200095.   DOI
2 S. M. Hong, A. K. Mutyala, and J. S. Park, "Synthesis and Optical Characterization of a Zinc-phthalocyanine Derivative Exhibiting High Solubility in Nonpolar Solvents", Text. Sci. Eng., 2016, 53, 379-384.   DOI
3 S. Vikneshvaran, J. W. Jang, N. N. T. Pham, S. J. Park, G. Balamurugan, S. G. Lee, and J. S. Park, "Near-infrared Absorption and Photothermal Properties of Heptamethine Pyrylium Dyes with Bistriflimide Anion", Dye. Pigm., 2022, 203, 110321.   DOI
4 V. Kumar, G. A. Baker, and S. Pandey, "Ionic Liquid-controlled J-versus H-aggregation of Cyanine Dyes", Chem. Commun., 2011, 47, 4730-4732.   DOI
5 Y. Cai, H. Zhu, Q. Shi, Y. Cheng, L. Chang, and W. Huang, "Photothermal Conversion of Ti2O3 Film for Tuning Terahertz Waves", iScience, 2022, 25, 103661.   DOI
6 A. Sebastian and E. Prasad, "Cyanide Sensing in Water Using a Copper Metallogel through "Turn-on" Fluorescence", Langmuir, 2020, 36, 35, 10537-10547.   DOI
7 M. Pengshung, E. D. Cosco, Z. Zhang, and E. M. Sletten, "Counterion Pairing Effect on a Flavylium Heptamethine Dye", Photochem. Photobiol., 2021, 98, 303-310.
8 J. L. Bricks, Y. L. Slominskii, I. D. Panas, and A. P. Demchenko, "Fluorescent J-aggregates of Cyanine Dyes: Basic Research and Applications Review", Methods Appl. Fluoresc., 2018, 6, 012001.
9 N. J. Hestand and F. C. Spano, "Expanded Theory of H- and JMolecular Aggregates: The Effects of Vibronic Coupling and Intermolecular Charge Transfer", Chem. Revterials, 2018, 118, 7069-7163.
10 J. Zemlicka and Z. Arnold, "Synthetic Reactions of Dimethylformamide. XI. Polyformylation of Ketones of other Types and the Problem of the Reaction Course", Collect. Czech. Chem. Commun., 1961, 26, 2852-2864.   DOI
11 G.-Y. Pan, H.-R. Jia, Y.-X. Zhu, R.-H. Wang, F.-G. Wu, and Z. Chen, "Dual Channel Activatable Cyanine Dye for Mitochondrial Imaging and Mitochondria-Targeted Cancer Theranostics", Sci. Eng., 2017, 3, 3596-3606.
12 G. Balamurugan and S. Velmathi, "Coplanarity Driven Fluorescence Turn-on Sensor for Chromium(iii) and Its Application for Bio-imaging", Photochem. Photobiol. Sci., 2018, 17, 239-244.   DOI