Improved Synthesis and Chromophoric Properties of Tetra-b-(2-octanyloxy)substituted Nickel Phthalocyanine

Fangdi Cong; Haifeng Wang; Jianxin Li; Lingling Li; Qianyun Yan; Xinxin Chu; Yanyan Meng; Kezhi Xing; Xiguang Du

doi:10.14233/ajchem.2014.15946

Issue

Vol. 26 No. 8 (2014): Vol 26 Issue 8

Issue Published : April 15, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Improved Synthesis and Chromophoric Properties of Tetra-b-(2-octanyloxy)substituted Nickel Phthalocyanine

https://doi.org/10.14233/ajchem.2014.15946

Fangdi Cong

Tianjin Key Laboratory of Aqua-ecology and Aquaculture, Department of Basic Science, Tianjin Agricultural University, Tianjin 300384, P.R. China

Haifeng Wang

Tianjin Key Laboratory of Aqua-ecology and Aquaculture, Department of Basic Science, Tianjin Agricultural University, Tianjin 300384, P.R. China

Jianxin Li

Faculty of Chemistry, Northeast Normal University, Changchun 130024, P.R. China

Lingling Li

Tianjin Key Laboratory of Aqua-ecology and Aquaculture, Department of Basic Science, Tianjin Agricultural University, Tianjin 300384, P.R. China

Qianyun Yan

Tianjin Key Laboratory of Aqua-ecology and Aquaculture, Department of Basic Science, Tianjin Agricultural University, Tianjin 300384, P.R. China

Xinxin Chu

Faculty of Chemistry, Northeast Normal University, Changchun 130024, P.R. China

Yanyan Meng

Faculty of Chemistry, Northeast Normal University, Changchun 130024, P.R. China

Kezhi Xing

Tianjin Key Laboratory of Aqua-ecology and Aquaculture, Department of Basic Science, Tianjin Agricultural University, Tianjin 300384, P.R. China

Xiguang Du

Faculty of Chemistry, Northeast Normal University, Changchun 130024, P.R. China

Corresponding Author(s) : Kezhi Xing

tn_aqua_lab@aliyun.com; xgdum@aliyun.com

Asian Journal of Chemistry, Vol. 26 No. 8 (2014): Vol 26 Issue 8
Article Published : April 16, 2014

Abstract

In order to further apprehend chromophoric properties of phthalcyanine materials, a lipophilic tetra-b-(2-octanyloxy)-substituted nickel phthalocyanine was synthesized with a yield of 78 % by a facile method without nitrogen protection and long-term heating performance. The synthetic compound was characterized by mass spectra, ¹H NMR, UV-visible, IR and elemental analysis, which were consistent with the proposed molecular structure. The compound not only behaved excellent solubility in many organic solvents, but also exhibited different chromophoric properties in various types of solvents, e.g., blue in isooctane and green in tetrahydrofuran. More interestingly, the chromophoric properties could be largely modulated by employed solvent, solution concentration and environment temperature.

Keywords

Phthalocyanine Synthesis Chromophoric property Modulation

Cong, F., Wang, H., Li, J., Li, L., Yan, Q., Chu, X., … Du, X. (2014). Improved Synthesis and Chromophoric Properties of Tetra-b-(2-octanyloxy)substituted Nickel Phthalocyanine. Asian Journal of Chemistry, 26(8), 2351–2356. https://doi.org/10.14233/ajchem.2014.15946

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References

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References

W. Li, A. Yu, D.C. Higgins, B.G. Llanos and Z. Chen, J. Am. Chem. Soc., 132, 17056 (2010); doi:10.1021/ja106217u.

T. Rawling and A. McDonagh, Coord. Chem. Rev., 251, 1128 (2007); doi:10.1016/j.ccr.2006.09.011.

M.G. Walter, A.B. Rudine and C.C. Wamser, J. Porphyr. Phthalocyanines, 14, 759 (2010); doi:10.1142/S1088424610002689.

J. Bartelmess, B. Ballesteros, G. de la Torre, D. Kiessling, S. Campidelli, M. Prato, T. Torres and D.M. Guldi, J. Am. Chem. Soc., 132, 16202 (2010); doi:10.1021/ja107131r.

L. Orzel, A. Janczyk, M. Brindell, G. Stopa and G. Stochel, J. Coord. Chem., 63, 2695 (2010); doi:10.1080/00958972.2010.507271.

H. Ali, S. Ait-Mohand, S. Gosselin, J.E. van Lier and B. Guérin, J. Org. Chem., 76, 1887 (2011); doi:10.1021/jo102083g.

Z. Ni, R. Li and J. Jiang, Struct. Bond., 133, 121 (2009); doi:10.1007/430_2008_13.

J. Mack and N. Kobayashi, Chem. Rev., 111, 281 (2011); doi:10.1021/cr9003049.

A.O. Naumov, E.V. Kudrik and G.P. Shaposhnikov, Chem. Heterocycl. Compd., 40, 469 (2004); doi:10.1023/B:COHC.0000033540.11478.9d.

D. Wróbel, A. Boguta and P. Mazurkiewicz, Spectrochim. Acta A, 59, 2841 (2003); doi:10.1016/S1386-1425(03)00083-0.

E.A. Cuellar and T.J. Marks, Inorg. Chem., 20, 3766 (1981); doi:10.1021/ic50225a039.

E.T. Saka, C. Göl, M. Durmus, H. Kantekin and Z. Biyiklioglu, J. Photochem. Photobiol. A, 241, 67 (2012); doi:10.1016/j.jphotochem.2012.05.023.

T. Nyokong, Coord. Chem. Rev., 251, 1707 (2007); doi:10.1016/j.ccr.2006.11.011.

H.I. Beltra’n, R. Esquivel, A. Sosa-Sa’nchez, J.L. Sosa-Sánchez, H. Höpfl, V. Barba, N. Farfán, M. Galicia García, O. Olivares-Xometl and L.S. Zamudio-Rivera, Inorg. Chem., 43, 3555 (2004); doi:10.1021/ic049634n.

L. Zhang, D. Qi, L. Zhao, Y. Bian and W. Li, J. Mol. Graph. Model., 35, 57 (2012); doi:10.1016/j.jmgm.2011.11.005.

Q. Cai, W. Zhu, H. Zhang, Y. Zhang and D. Ma, Synthesis, 741 (2005); doi:10.1055/s-2004-831196.

F.D. Cong, B. Ning, X.G. Du, C.Y. Ma, H.F. Yu and B. Chen, Dyes Pigments, 66, 149 (2005); doi:10.1016/j.dyepig.2004.09.016.

N.S. Lebedeva, E.V. Trofimova, N.A. Pavlycheva and A.I. Vyugin, Russ. J. Org. Chem., 38, 1195 (2002); doi:10.1023/A:1020965913255.

A. Günsel, M.N. Yaraşir, M. Kandaz and A. Koca, Polyhedron, 29, 3394 (2010); doi:10.1016/j.poly.2010.09.035.

N.S. Lebedeva, N.A. Pavlycheva, E.V. Parfenyuk and A.I. Vyugin, J. Chem. Thermodyn., 38, 165 (2006); doi:10.1016/j.jct.2005.04.001.

Issue

Vol. 26 No. 8 (2014): Vol 26 Issue 8

Improved Synthesis and Chromophoric Properties of Tetra-b-(2-octanyloxy)substituted Nickel Phthalocyanine

Corresponding Author(s) : Kezhi Xing

Abstract

Keywords

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