Textile Coloration and Finishing (한국염색가공학회지)

The Korean Society of Dyers and Finishers (한국염색가공학회)
권호 표지
DOI QR코드

DOI QR Code

Efficient Fluorescence Quenching of tert-butyl substituted Phthalocyanines with Picric Acid

  • Gupta, Ankush (Department of Organic Material and Polymer Engineering, Dong-A University) ;
  • Kim, Meena (Department of Organic Material and Polymer Engineering, Dong-A University) ;
  • Park, Jong S. (Department of Organic Material and Polymer Engineering, Dong-A University)
  • Received : 2014.10.10
  • Accepted : 2014.12.18
  • Published : 2014.12.27
Download PDF
⟨ Previous Next ⟩

Abstract

Two tert-butyl substituted phthalocyanines(Pcs), in metal-free and metallated forms, were synthesized and the fluorescence responses toward various nitro derivatives, including picric acid(PA), 2,4-dinitrotoluene(DNT), 1,4-dinitrobenzene(DNB), 4-nitrotoluene(NT), nitrobenzene(NB), 1,4-benzoquinone(BQ), and nitromethane(NM) were investigated. Among the various nitro derivatives, current Pc derivatives exhibited efficient and exclusive fluorescence quenching in the presence of picric acid, which was readily observed by a naked eye. Quenching efficiency was estimated by the Stern-Volmer relationship, in which quenching constant, KSV, was calculated to be in the range of $10^4M^{-1}$. It was also found out that the aggregational behaviors of these Pcs are heavily dependent on the nature of solvent systems, subsequently affecting the quenching efficiency.

Keywords

References

  1. S. W. Thomas, G. D. Joly, and T. M. Swager, Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers, Chem Rev, 107, 1339(2007). https://doi.org/10.1021/cr0501339
  2. Y. Hong, J. W. Y. Lam, and B. Z. Tang, Aggregation-Induced Emission, Chem Soc Rev, 40, 5361(2011). https://doi.org/10.1039/c1cs15113d
  3. D. S. Moore, Instrumentation for Trace Detection of High Explosives, Rev Sci Instrum, 75, 2499(2004). https://doi.org/10.1063/1.1771493
  4. D. T. Mcquade, A. E. Pullen, and T. M. Swager, Conjugated Polymer-Based Chemical Sensors, Chem Rev, 100, 2537(2000). https://doi.org/10.1021/cr9801014
  5. A. Fainberg, Explosives Detection for Aviation Security, Science, 255, 1531(1992). https://doi.org/10.1126/science.255.5051.1531
  6. M. E. Germain and M. J. Knapp, Discrimination of Nitroaromatics and Explosives Mimics by a Fluorescent Zn(salicyaldimine) Sensor Array, J. Am Chem Soc, 130, 5422(2008). https://doi.org/10.1021/ja800403k
  7. J. Shen, J. Zhang, Y. Zuo, L. Wang, X. Sun, J. Li, W. Han, and R. J. He, Biodegradation of 2,4,6-trinitrophenol by Rhodococcus sp. Isolated from a Picric Acid Contaminated Soil, Hazard Mater, 163, 1199(2009). https://doi.org/10.1016/j.jhazmat.2008.07.086
  8. Y. Peng, A. J. Zhang, M. Dong, and Y. W. Wang, A Colorimetric and Fluorescent Chemosensor for the Detection of an Explosive-2,4,6-trinitrophenol, Chem Commun, 47, 4505(2011). https://doi.org/10.1039/c1cc10400d
  9. C. C. Leznoff and A. B. P. Lever, "Phthalocyanines, Properties and Applications", VCH, NY, Vol.1-3, pp.1988-1993, 1996.
  10. J. U. Lee, Y. D. Kim, J. W. Jo, J. P. Kim, and W. H. Jo, Efficiency Enhancement of P3HT/PCBM Bulk Heterojunction Solar Cells by Attaching Zinc Phthalocyanine to the Chain-end of P3HT, J. Mater Chem, 21, 17209(2011). https://doi.org/10.1039/c1jm11563d
  11. E. M. Maya, P. Vazquez, and T. Torres, Synthesis of Alkynyl-Linked Phthalocyanine Dyads: Push-Pull Homo and Heterodimetallic Bisphthalocyaninato Complexes, Chem Eur J., 5, 2004(1999). https://doi.org/10.1002/(SICI)1521-3765(19990702)5:7<2004::AID-CHEM2004>3.0.CO;2-P
  12. Z. Hao, X. Wu, R. Sun, C. Ma, and X. Zhang, Morphology Controlled Nanostructures Self-Assembled from Phthalocyanine Derivatives Bearing Alkylthio Moieties: Effect of Sulfur-Sulfur and Metal-Ligand Coordination on Intermolecular Stacking, Chem Phys Chem, 13, 267(2012). https://doi.org/10.1002/cphc.201100612
  13. S. S. Nagarkar, B. Joarder, A. K. Chaudhari, S. Mukherjee, and S. K. Ghosh, Highly Selective Detection of Nitro Explosives by a Luminescent Metal-Organic Framework, Angew Chem Int Ed, 52, 2881(2013). https://doi.org/10.1002/anie.201208885
  14. H. Sohn, R. M. Calhoun, M. J. Sailor, and W. C. Trogler, Detection of TNT and Picric Acid on Surfaces and in Seawater by Using Photoluminescent Polysiloles, Angew Chem Int Ed, 40, 2104(2001). https://doi.org/10.1002/1521-3773(20010601)40:11<2104::AID-ANIE2104>3.0.CO;2-#
  15. X. Zhang, D. Gao, J. Gao, P. Zhu, M. Bouvet, and Y. Chen, Morphology Controlled Nano-Structures of an Octa(phenoxy)-Substituted Phthalocyaninato Zinc Complex: Solvent Effect on the Self-Assembly Behaviour, RSC Adv, 4, 14807(2014). https://doi.org/10.1039/c3ra44687e
  16. B. Z. Tang, Y. Geng, J. W. Y. Lam, B. Li, X. Jing, X. Wang, F. Wang, A. B. Pakhomov, and X. Zhang, Processible Nanostructured Materials with Electrical Conductivity and Magnetic Susceptibility: Preparation and Properties of Maghemite/Polyaniline Nanocomposite Films, Chem Mater, 11, 1581(1999). https://doi.org/10.1021/cm9900305
  17. J. Wang, J. Mei, W. Yuan, P. Lu, A. Qin, J. Sun, Y. Ma, and B. Z. Tang, Hyperbranched Polytriazoles with High Molecular Compressibility: Aggregation-induced Emission and Superamplified Explosive Detection, J. Mater Chem, 21, 4056(2011). https://doi.org/10.1039/c0jm04100a

Cited by

  1. Characteristics and Application of the Highly-Durable and Highly-Sensitive Super Hydrophobic Acid-gas Sensing Dye vol.27, pp.2, 2015, https://doi.org/10.5764/TCF.2015.27.2.105
  2. Effects of Surfactants on Dispersion Behavior of Vectran®in Water(II) -Study on the Manufacture and Properties of Wet-laid Nonwoven Fabrics- vol.27, pp.4, 2015, https://doi.org/10.5764/TCF.2015.27.4.327