Textile Science and Engineering (한국섬유공학회지)

The Korean Fiber Society (한국섬유공학회)
권호 표지
DOI QR코드

DOI QR Code

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

다양한 대이온을 가지는 헵타메틴계 인돌린 시아닌 염료의 합성과 광학 특성 연구

  • 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)
  • 박세정 (부산대학교 응용화학공학부) ;
  • 고팔 발라무루간 (부산대학교 응용화학공학부) ;
  • 장재웅 (부산대학교 응용화학공학부) ;
  • 박종승 (부산대학교 응용화학공학부)
  • Received : 2022.09.19
  • Accepted : 2022.10.24
  • Published : 2022.10.31
⟨ Previous Next ⟩

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

Acknowledgement

이 논문은 부산대학교 기본연구지원사업(2년)에 의하여 연구되었음.

References

  1. 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.
  2. 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. https://doi.org/10.1016/j.dyepig.2022.110321
  3. 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.
  4. 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.
  5. V. Kumar, G. A. Baker, and S. Pandey, "Ionic Liquid-controlled J-versus H-aggregation of Cyanine Dyes", Chem. Commun., 2011, 47, 4730-4732. https://doi.org/10.1039/c1cc00080b
  6. 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. https://doi.org/10.1135/cccc19612852
  7. 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. https://doi.org/10.1016/j.isci.2021.103661
  8. 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. https://doi.org/10.1002/ajoc.202200095
  9. 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. https://doi.org/10.1039/c7pp00425g
  10. A. Sebastian and E. Prasad, "Cyanide Sensing in Water Using a Copper Metallogel through "Turn-on" Fluorescence", Langmuir, 2020, 36, 35, 10537-10547. https://doi.org/10.1021/acs.langmuir.0c01803
  11. 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. https://doi.org/10.12772/TSE.2016.53.379
  12. 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.