Download PDF
Synthesis 2021; 53(15): 2656-2664
DOI: 10.1055/a-1499-8865
paper

Facile, Mild-Temperature Synthesis of Metal-Free Phthalocyanines

Fangdi Cong‡
a   Faculty of Chemistry, Northeast Normal University, Renmin Street No. 5268, Changchun 130024, P. R. of China
b   Tianjin Key Laboratory of Aqua-ecology and Aquaculture, College of Basic Science, Tianjin Agricultural University, Jinjing Road No. 22, Tianjin 300392, P. R. of China
,
Hongzhen Jiang‡
b   Tianjin Key Laboratory of Aqua-ecology and Aquaculture, College of Basic Science, Tianjin Agricultural University, Jinjing Road No. 22, Tianjin 300392, P. R. of China
,
Xiguang Du∗
a   Faculty of Chemistry, Northeast Normal University, Renmin Street No. 5268, Changchun 130024, P. R. of China
,
Wei Yang
b   Tianjin Key Laboratory of Aqua-ecology and Aquaculture, College of Basic Science, Tianjin Agricultural University, Jinjing Road No. 22, Tianjin 300392, P. R. of China
,
Shulin Zhang∗
b   Tianjin Key Laboratory of Aqua-ecology and Aquaculture, College of Basic Science, Tianjin Agricultural University, Jinjing Road No. 22, Tianjin 300392, P. R. of China
› Author AffiliationsWe gratefully thank the National Natural Science Foundation of China (20472014), the Jilin Provincial Development and Re-form Commission Project (2019C040), the National Key Research and Development Program of China (2019YFC1605305-03), the Key Project of Tianjin Natural Science Foundation (18JCZDJC97800) and the Open Fund of Tianjin Key Lab of Aquatic Ecology and Aquaculture (TJAE201802), for their support.
› Further Information
    Permissions and Reprints All articles of this category


Abstract

It is important for the synthesis and research of phthalocyanine compounds for these compounds to be easily obtained at low temperature. We observed that metal-free phthalocyanine was sometimes found in a simple system used to synthesize phthalocyanine precursors at room temperature, and further studies showed that the key to the effective formation of phthalocyanines at low temperature lay in the presence of equal volumes of alcohol and amine, in addition to substrate phthalonitriles and solvents, in the reaction system. A synthetic mechanism was proposed and facile syntheses have been realized, such as the synthesis of tetra-α(β)-nitrophthalocyanines and tetra-α(β)-(4-tert-butylphenoxy)phthalocyanines from the corresponding substituted phthalonitriles at mild temperature (37 °C). The results are significant for the design and synthesis of new phthalocyanine derivatives, and the method is convenient and easy to adopt for general use in standard laboratories.

Key words

metal-free phthalocyanine - facile synthesis - characterization - room temperature - amine - alcohol - phthalonitrile

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1499-8865.
  • Supporting Information


Publication History

Received: 25 March 2021

Accepted after revision: 05 May 2021

Accepted Manuscript online:
05 May 2021

Article published online:
25 May 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Garip E. Ö, Özçeşmeci M, Katırcı R, Özçeşmeci İ, Hamuryudan E. J. Porphyrins Phthalocyanines 2019; 23: 1563
    Crossref
  • 2 Shiina Y, Kage Y, Furukawa K, Wang H, Yoshikawa H, Furuta H, Kobayashi N, Shimizu S. Angew. Chem. Int. Ed. 2020; 132: 22910
    Crossref
  • 3 Winterfeld KA, Lavarda G, Guilleme J, Sekita M, Guldi DM, Torres T, Bottari G. J. Am. Chem. Soc. 2017; 139: 5520
    CrossrefPubMed
  • 4 Huang X, Hu M, Zhao X, Li C, Yuan Z, Liu X, Cai C, Zhang Y, Hu Y, Chen Y. Org. Lett. 2019; 21: 3382
    CrossrefPubMed
  • 5 Braun A, Tcherniac J. Ber. Dtsch. Chem. Ges. 1907; 40: 2709
    Crossref
  • 6 Cao L, Fei X, Zhao H, Huang C. Dyes Pigm. 2019; 173: 107879
    Crossref
  • 7 Janczak J. Polyhedron 2014; 70: 164
    Crossref
  • 8 Gsänger M, Bialas D, Huang L, Stolte M, Würthner F. Adv. Mater. 2016; 28: 3615
    CrossrefPubMed
  • 9 Peng J, Huang Q, Zhuge W, Liu Y, Zhang C, Yang W, Xiang G. Biosens. Bioelectron. 2018; 106: 212
    CrossrefPubMed
  • 10 Winiarski JP, de Barros MR, Wecker GS, Nagurniak GR, Parreira RL. T, Affeldt RF, Peralta RA, Jost CL. J. Mater. Chem. C 2020; 8: 6839
    Crossref
  • 11 Castro KA. D. F, Figueira F, Almeida Paz FA, Tome JP. C, da Silva RS, Nakagaki S, Neves MG. P. M. S, Cavaleiro JA. S, Simões MM. Q. Dalton Trans. 2019; 8144
    CrossrefPubMed
  • 12 Bian J, Feng J, Zhang Z, Li Z, Zhang Y, Liu Y, Ali S, Qu Y, Bai L, Xie J, Tang D, Li X, Bai F, Tang J, Jing L. Angew. Chem. Int. Ed. 2019; 58: 10873
    CrossrefPubMed
  • 13 Nezhad ZA. R, Reza MM, Sefidan JM. F, Yousef F, Habib T, Reza R. Laser Med. Sci. 2018; 33: 1969
    CrossrefPubMed
  • 14 Bayat F, Karimi AR. Int. J. Biol. Macromol. 2019; 129: 927
    CrossrefPubMed
  • 15 Wong CT. T, Chu JC. H, Ha SY. Y, Wong RC. H, Dai G, Kwong T, Wong C, Ng DK. P. Org. Lett. 2020; 22: 7098
    CrossrefPubMed
  • 16 Lu X, Zhu W, Chen T, Peng Q, Yu C, Yang M. Chem. Phys. Lett. 2019; 735: 136737
    Crossref
  • 17 Cong FD, Ning B, Du XG, Ma CY, Yu HF, Chen B. Dyes Pigm. 2005; 66: 149
    Crossref
  • 18 Ma C, Tian D, Hou X, Chang Y, Cong F, Yu H, Du X, Du G. Synthesis 2005; 741
  • 19 Leznoff CC, Hu M, Nolan KJ. M. Chem. Commun. 1996; 27: 1245
    Crossref
  • 20 Kharisov BI, Cantú Coronado CE, Coronado Cerda KP, Ortiz Méndez U, Jacobo Guzmán JA, Ramírez Patlán LA. Inorg. Chem. Commun. 2004; 7: 1269
    Crossref
  • 21 Garnovskii AD, Kharisov BI. Synthetic Coordination and Organometallic Chemistry . Marcel Dekker Inc; New York: 2003: 513
    CrossrefGoogle Scholar
  • 22 Nemykin VN, Kobayashi N, Mytsyk VM, Volkov SV. Chem. Lett. 2000; 29: 546
    Crossref
  • 23 Kharisov BI, Ortiz Méndez U, Almaraz Garza JL, Almaguer Rodríguez JR. New J. Chem. 2005; 29: 686
    Crossref
  • 24 Kharisov BI, Rivera de la Rosa J, Kharissova OV, Almaraz Garza JL, Almaguer Rodríguez JR, Puente LI, Ortiz Méndez U, Ibarra Arvizu AK. J. Coord. Chem. 2007; 60: 355
    Crossref
  • 25 Cong F, Wei Z, Huang Z, Yu F, Liu H, Cui J, Yu H, Chu X, Du X, Xing K, Lai J. Dyes Pigm. 2015; 120: 1
    Crossref
  • 26 Furuyama T, Maeda K, Maeda H, Segi M. J. Org. Chem. 2019; 84: 14306
    CrossrefPubMed
  • 27 Mohammed I, Oluwole DO, Nemakal M, Sannegowda LK, Nyokong T. Dyes Pigm. 2019; 170: 107592
    Crossref
  • 28 Bachovchin WW. Magn. Reson. Chem. 2001; 39: S199
    Crossref
  • 29 Dudiak BM, Maksimchuk KR, Bednar MM, Podracky CJ, Burg JM, Nguyen TM, Nwogbo FO, Valdivia RH, Mccafferty DG. Biochemistry 2019; 58: 3527
    CrossrefPubMed
  • 30 Zhang C, Bijl E, Svensson B, Hettinga K. Compr. Rev. Food Sci. F. 2019; 18: 834
    CrossrefPubMed
  • 31 Tomoda H, Saito S, Ogawa S, Shiraishi S. Chem. Lett. 1980; 9: 1277
    Crossref
  • 32 Elleuche S, Fodor K, von der Heyde A, Klippel B, Wilmanns M, Antranikian G. Appl. Microbiol. Biotechnol. 2013; 97: 8963
    CrossrefPubMed
  • 33 Schwander T, Mclean R, Zarzycki J, Erb TJ. J. Biol. Chem. 2018; 293: 1702
    CrossrefPubMed
  • 34 Yamada Y, Nawate K, Maeno T, Tanaka K. Chem. Commun. 2018; 54: 8226
    CrossrefPubMed
  • 35 Li P, Cong F, Zhang S, Zhou W, Zhu H, Xu Y, Yu J. Anal. Methods 2019; 11: 5629
    Crossref
  • 36 Leznoff CC, Hu M, Mcarthur CR, Qing Y, van Lier JE. Can. J. Chem. 1994; 72: 1990
    Crossref
  • 37 Kasuga K, Kawashima M, Asano K, Sugimori T, Abe K, Kikkawa T, Fujiwara T. Chem. Lett. 1996; 25: 867
    Crossref
  • 38 Kobayashi N, Narita F, Ishii K, Muranaka A. Chem. Eur. J. 2009; 15: 10173
    CrossrefPubMed
  • 39 Makhseed S, Tuhl A, Samuel J, Zimcik P, Al-Awadi N, Novakova V. Dyes Pigm. 2012; 95: 351
    Crossref
  • 40 Durmus M, Nyokong T. Polyhedron 2007; 26: 2767
    Crossref