Citation: OGUNSIPE Abimbola, NYOKONG Tebello. Solvent Effects on the Photophysicochemical Properties of Tetra(tert-butylphenoxy)phthalocyaninato Zinc(II)[J]. Acta Physico-Chimica Sinica, ;2011, 27(05): 1045-1052. doi: 10.3866/PKU.WHXB20110508 shu

Solvent Effects on the Photophysicochemical Properties of Tetra(tert-butylphenoxy)phthalocyaninato Zinc(II)

OGUNSIPE Abimbola ¹ ,
NYOKONG Tebello ^2,

1.
1. Department of Chemistry, Kwara State University, Malete; P.M.B 1530, Ilorin, Nigeria;
2. Department of Chemistry, Rhodes University, Grahamstown 6140, South Africa

Received Date: 9 December 2010
Available Online: 28 March 2011
Fund Project: The project was supported by the Department of Science and Technology (DST) (DST)National Research Foundation (NRF) of South Africa through DST/NRF South African Research Chairs Initiative for Professor of Medicinal Chemistry and Nanotechnology and Rhodes University. (NRF)

The solvent viscosity dependence of the photophysical and photochemical properties of tetra(tert-butylphenoxy)phthalocyaninato zinc(II) (ZnTBPPc) is presented. The fluorescence quantum yields (Φ_F) and Stern-Volmer′s constant (K_SV) for ZnTBPPc fluorescence quenching by benzoquinone in all the solutions followed a semi-empirical law that depends only on the solvent viscosity. Φ_F values vary between 0.08 in tetrahydrofuran (THF) and 0.14 in dimethylsulphoxide (DMSO). Triplet quantum yields (Φ_T) and lifetimes (τ_T) also exhibit clear solvent viscosity dependence with the values being higher in the most viscous solvents. The interaction of the ZnTBPPc triplet state with oxygen was found to be diffusion- controlled, but higher rate constants were observed in low-viscosity solvents like THF and toluene. Absolute values of singlet oxygen quantum yields (Φ_Δ) were determined, and the values are comparable in all the solvents, which is attributed to the proximity of the ZnTBPPc triplet energies in different solvents.
- Phthalocyanine,
- Solvent,
- Viscosity,
- Fluorescence,
- Triplet state,
- Singlet oxygen
1. [1]
  
  (1) Leznoff, C. C.; Lever, A. B. P. The Phthalocyanines: Properties and application, 1st ed.; Wiley: USA, 1986-1993.
2. [2]
  (2) Mckeown, N. B. Phthalocyanine Materials—Synthesis, Structure and Function; Cambridge University Press: Cambridge, 1998.
3. [3]
  (3) Kadish, K.; Smith, K. M.; Guilard, R. The Porphyrin Handbook; Academic Press: Boston, 2003.
4. [4]
  (4) Nyokong, T.; Vilakazi, S. TALANTA 2003, 61, 27.
5. [5]
  (5) Arguello, J.; Ma sso, H. A.; Landers, R.; Gushikem, Y. J. Electroanal. Chem. 2008, 617, 45.
6. [6]
  (6) Wang, Z.; Mao, W.; Chen, H.; Zhang, F.; Fan, X.; Qian, G. Catl. Commun. 2006, 7, 518.
7. [7]
  (7) Iliev, V.; Alexiev, V.; Bilyarska, L. J. Mol. Catl. A: Chem. 1999, 137, 15.
8. [8]
  (8) Brasseur, N.; Ooellet, R.; Madeleine, C. L.; Van Lier, J. E. Br. J. Cancer 1999, 80, 1533.
9. [9]
  (9) MacDonald, I. J.; Dougherty, T. J. J. Porphyrins Phthalocyanines 2001, 5, 105.
10. [10]
  (10) Vrouenraets, M. B.; Visser, G. W. M.; Stigter, M.; Oppelaar, H.; Snow, G. B.; Van Dongen, G. A. M. S. Cancer Res. 2001, 61, 1970.
11. [11]
  (11) Zhao, Z.; Ogunsipe, A. O.; Maree, M. D.; Nyokong, T. J. Porphyrins Phthalocyanines 2005, 9, 186.
12. [12]
  (12) Yang, S. I.; Li, J.; Cho, H. S.; Kin, D.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Mater. Chem. 2000, 10, 283.
13. [13]
  (13) Kimura, M.; Nakada, K.; Yamaguchi, Y.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Commun. 1997, 1215.
14. [14]
  (14) Wiederkehr, N. A. J. Braz. Chem. Soc. 1996, 7, 7.
15. [15]
  (15) Ogunsipe, A.; Maree, D.; Nyokong, T. J. Mol. Struc. 2003, 650, 131.
16. [16]
  (16) Ogunsipe, A.; Chen, J. Y.; Nyokong, T. New J. Chem. 2004, 28, 822.
17. [17]
  (17) Beeby, A.; Parker, A. W.; Simpson, M. S. C.; Phillips, D. J. Photochem. Photobiol. B: Biol. 1992, 16, 73.
18. [18]
  (18) Metz, J.; Schneider, O.; Hanack, M. Inorg. Chem. 1984, 23, 1065.
19. [19]
  (19) Fery-Forgues, S.; Lavabre, D. J. Chem. Ed. 1999, 76, 1260.
20. [20]
  (20) Maree, S.; Phillips, D.; Nyokong, T. J. Porphyrins Phthalocyanines 2002, 6, 17.
21. [21]
  (21) Montalban, A.; Meunier, H.; Ostler, R.; Barrett, A.; Hoffman, B.; Rumbles, G. J. Phys. Chem. A. 1999, 103, 4352.
22. [22]
  (22) Lakowikz, J. R. Principles of Fluorescence Spectroscopy, 2nd ed; Kluwer Academic/Plenum Publishers: New York, 1999.
23. [23]
  (23) Kubát, P.; Mosinger, J. J. Photochem. Photobiol. A: Chem., 1996, 96, 93.
24. [24]
  (24) Kossanyi, J.; Chahraoui, D. Int. J. Photoenergy 2000, 2, 9.
25. [25]
  (25) Tran-Thi, T. H.; Desforge, C.; Thiec, C. J. Phys. Chem. 1989, 93, 1226.
26. [26]
  (26) Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of photochemistry, 2nd ed.; M. Decker: New York, 1993.
27. [27]
  (27) Law, W. F.; Liu, R. C. W.; Jiang, J.; Ng, D. K. P. Inorg. Chim. Acta 1997, 256, 147.
28. [28]
  (28) Isa , H.; Kagaya, Y.; Matsushita, A. Chem. Lett. 2004, 33, 862.
29. [29]
  (29) Naumov, A. O.; Kudrik, E. V.; Shaposhnikov, G. P. Chem. Hetero Compds. 2004, 40, 469.
30. [30]
  (30) Ogunsipe, A.; Mahmut, M.; Atilla, D.; Gürek, A. G.; Ahsen, V.; Nyokong, T. Synth. Metals 2008, 158, 839.
31. [31]
  (31) Natarajan, L. V.; Ricker, J. E.; Blankenship, R. E.; Chang, R. Photochem. Photobiol. 1984, 39, 301.
32. [32]
  (32) Mills, A.; Thomas, M. D. Analyst 1998, 123, 1135.
33. [33]
  (33) Losev, A. P.; Volkovich, D. I.; Tikhomirov, S. A. J. Appl. Spec. 1999, 66, 11.
34. [34]
  (34) Bunce, N. J.; Hadley, M. Can. J. Chem. 1975, 53, 3240.
35. [35]
  (35) Idowu, M.; Ogunsipe, A.; Nyokong, T. Spectrochim. Acta A 2007, 68, 995.
36. [36]
  (36) Georghiou, S.; Gerke, L. S. Photochem. Photobiol. 1999, 69, 646.
37. [37]
  (37) Taylor, J. R.; Adams, M. C.; Sibbett, W. Appl. Phys. B: Lasers and Optics 1980, 21, 13.
38. [38]
  (38) F?rster, T.; Hoffmann, G. Z. Phys. Chem. 1971, 75, 63.
39. [39]
  (39) Smith, G. J. J. Chem. Soc. Faraday Trans. 2 1982, 78, 769.
40. [40]
  (40) Battino, R. Solubility Data Series; Pergamon Press: Oxford, 1981.
41. [41]
  (41) Rios, A. O.; Mercadante, A. Z.; Borsarelli, C. D. Dyes and Pigments 2007, 74, 561.
42. [42]
  (42) Turro, N. J. Modern Molecular Photochemistry; University Science Books: California, 1991.
43. [43]
  (43) Spiller, W.; Kliesch, H.; Wohrle, D.; Hackbarth, S.; Roder, B.; Schnurpfeil, G. J. Porphyrins Phthalocyanines 1998, 2, 145.
44. [44]
  (44) Hurst, J. R.; McDonald, J. D.; Schuster, G. B. J. Am. Chem. Soc. 1982, 104, 2065.
45. [45]
  (45) Okamoto, M.; Tanaka, F. J. Phys. Chem. 1993, 97, 177.
46. [46]
  (46) Aveline, B.; Delgado, O.; Brault, D. J. Chem. Soc. Faraday Trans. 1992, 88, 1971.
47. [47]
  (47) Fuke, K.; Ueda, M.; Itoh, M. J. Am. Chem. Soc. 1983, 105, 1091.
48. [48]
  (48) Nilsson, R.; Kearns, D. R. J. Phys. Chem. 1974, 78, 1681.
1. [1]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
2. [2]
  Chen Lu , Zefeng Yu , Jing Cao . Advancement in porphyrin/phthalocyanine compounds-based perovskite solar cells. Chinese Journal of Structural Chemistry, 2024, 43(3): 100240-100240. doi: 10.1016/j.cjsc.2024.100240
3. [3]
  Ying Xu , Chengying Shen , Hailong Yuan , Wei Wu . Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting. Chinese Chemical Letters, 2024, 35(9): 109324-. doi: 10.1016/j.cclet.2023.109324
4. [4]
  Lanyun Zhang , Weisi Wang , Yu-Qiang Zhao , Rui Huang , Yuxun Lu , Ying Chen , Liping Duan , Ying Zhou . Mechanism study of the molluscicide candidate PBQ on Pomacea canaliculata using a viscosity-sensitive fluorescent probe. Chinese Chemical Letters, 2025, 36(1): 109798-. doi: 10.1016/j.cclet.2024.109798
5. [5]
  Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876
6. [6]
  Deshuai Zhen , Chunlin Liu , Qiuhui Deng , Shaoqi Zhang , Ningman Yuan , Le Li , Yu Liu . A review of covalent organic frameworks for metal ion fluorescence sensing. Chinese Chemical Letters, 2024, 35(8): 109249-. doi: 10.1016/j.cclet.2023.109249
7. [7]
  Manman Ou , Yunjian Zhu , Jiahao Liu , Zhaoxuan Liu , Jianjun Wang , Jun Sun , Chuanxiang Qin , Lixing Dai . Polyvinyl alcohol fiber with enhanced strength and modulus and intense cyan fluorescence based on covalently functionalized graphene quantum dots. Chinese Chemical Letters, 2025, 36(2): 110510-. doi: 10.1016/j.cclet.2024.110510
8. [8]
  Junqing Wu , Yiyang Zhang , Qingqing Hong , Hui Yang , Lifeng Zhang , Ming Zhang , Lei Yu . Organometallic modification of silica with europium endowing the fluorescence properties: The key technique for numerical quality monitoring. Chinese Chemical Letters, 2025, 36(4): 110165-. doi: 10.1016/j.cclet.2024.110165
9. [9]
  Wenzhong Zhang , Zirui Yan , Lingcheng Chen , Yi Xiao . Sn-fused perylene diimides: Synthesis, mechanism, and properties. Chinese Chemical Letters, 2024, 35(10): 109582-. doi: 10.1016/j.cclet.2024.109582
10. [10]
  Cheng He , Renlan Huang , Lingling Wei , Qiuhui He , Jinbo Liu , Jiao Chen , Ge Gao , Cheng Yang , Wanhua Wu . Uncovering the mask of sensitizers to switch on the TTA-UC emission by supramolecular host-guest complexation. Chinese Chemical Letters, 2025, 36(4): 110103-. doi: 10.1016/j.cclet.2024.110103
11. [11]
  Wei Su , Xiaoyan Luo , Peiyuan Li , Ying Zhang , Chenxiang Lin , Kang Wang , Jianzhuang Jiang . Phthalocyanine self-assembled nanoparticles for type Ⅰ photodynamic antibacterial therapy. Chinese Chemical Letters, 2024, 35(12): 109522-. doi: 10.1016/j.cclet.2024.109522
12. [12]
  Shenghui Tu , Anru Liu , Hongxiang Zhang , Lu Sun , Minghui Luo , Shan Huang , Ting Huang , Honggen Peng . Oxygen vacancy regulating transition mode of MIL-125 to facilitate singlet oxygen generation for photocatalytic degradation of antibiotics. Chinese Chemical Letters, 2024, 35(12): 109761-. doi: 10.1016/j.cclet.2024.109761
13. [13]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
14. [14]
  Mengfan Zhang , Lingyan Liu , Peng Wei , Wei Feng , Tao Yi . A proximity tagging strategy utilizing an activated aldehyde group as the active site. Chinese Chemical Letters, 2025, 36(4): 110127-. doi: 10.1016/j.cclet.2024.110127
15. [15]
  Ying Wang , Hong Yang , Caixia Zhu , Qing Hong , Xuwen Cao , Kaiyuan Wang , Yuan Xu , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Cascading oxidoreductases-like nanozymes for high selective and sensitive fluorescent detection of ascorbic acid. Chinese Chemical Letters, 2025, 36(4): 110153-. doi: 10.1016/j.cclet.2024.110153
16. [16]
  Yan Zhu , Jia Liu , Meiheng Lv , Tingting Wang , Dongxiang Zhang , Rong Shang , Xin-Dong Jiang , Jianjun Du , Guiling Wang . Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation. Chinese Chemical Letters, 2024, 35(10): 109446-. doi: 10.1016/j.cclet.2023.109446
17. [17]
  Shuai Qiu , Jia He , Xiao Hu , Hongxia Yan , Zhao Gao , Wei Tian . Cation-π enhanced triplet-to-singlet Förster resonance energy transfer for fluorescence afterglow. Chinese Chemical Letters, 2025, 36(4): 110057-. doi: 10.1016/j.cclet.2024.110057
18. [18]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
19. [19]
  Chi Zhang , Ning Ding , Yuwei Pan , Lichun Fu , Ying Zhang . The degradation pathways of contaminants by reactive oxygen species generated in the Fenton/Fenton-like systems. Chinese Chemical Letters, 2024, 35(10): 109579-. doi: 10.1016/j.cclet.2024.109579
20. [20]
  Meiling Xu , Xinyang Li , Pengyuan Liu , Junjun Liu , Xiao Han , Guodong Chai , Shuangling Zhong , Bai Yang , Liying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860

Get Citation

PDF

XML

Metrics

PDF Downloads(1440)
Abstract views(2191)
HTML views(27)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142