Chinese Journal of Organic Chemistry >
Research Progress in Synthesis, Properties and Application of Subphthalocyanine
Received date: 2022-11-16
Revised date: 2023-01-27
Online published: 2023-03-31
Supported by
The Natural Science Foundation of Jiangsu Province(BK20210876); The Natural Science Foundation of the Jiangsu Higher Education Institutions(20KJB150013)
Subphthalocyanine, as a typical contracted analogue of phthalocyanine, exhibits novel cone structure, excellent luminescent properties and high flexibility of modification, which enables it as a new type of fluorescent dye with great research prospects. It has been proved that simple modifications of the axial, peripheral or central ring structure of subphthalocyanine can effectively regulate its physical and chemical properties, such as solubility, absorption/fluorescence emission, fluorescence quantum yield and singlet oxygen yield, and these properties have attracted extensive attentions from chemists in recent years. This review introduces the structures, properties and research significance of subphthalocyanine. Then, the progress in the synthesis, the relationship between properties and molecular structure of subphthalocyanin, and their applications in the area of biochemistry, material chemistry and environmental chemistry are reviewed emphatically. Finally, the development status of subphthalocyanine is summarized, and the further development of subphthalocyanine is discussed and proposed.
Key words： subphthalocyanine; structures; photoelectric properties; application
Shutong Zhou , Shengnan Tu , Zijian Gao , Yemei Wang , Shasha Sun . Research Progress in Synthesis, Properties and Application of Subphthalocyanine[J]. Chinese Journal of Organic Chemistry, 2023 , 43(8) : 2628 -2646 . DOI: 10.6023/cjoc202211020
| [1] | Meller, A.; Ossko, A. Monatsh. Chem. 1972, 103, 150. |
| [2] | Rauschnabe, J.; Hanack, M. Tetrahedron Lett. 1995, 36, 1629. |
| [3] | Claessens, C. G.; Gonzalez-Rodriguez, D.; Rodriguez-Morgade, M. S.; Medina, A.; Torres, T. Chem. Rev. 2014, 114, 2192. |
| [4] | Claessens, C. G.; Gonzalez-Rodriguez, D.; Torres, T. Chem. Rev. 2002, 102, 835. |
| [5] | Liu, W.; Lee, C. H.; Li, H. W.; Lam, C. K.; Wang, J.-Z.; Mak, T. C.; Ng, D. K. P. Chem. Commun. 2002, 6, 628. |
| [6] | Li, D.-P.; Zhang, P.; Ge, S.-X.; Sun, G.-F.; He, Q.; Fa, W.-J.; Li, Y.; Ma, J.-T. RSC Adv. 2021, 11, 31226. |
| [7] | Yuan, Y.-B.; Li, H.; Jiang, Z.; Lin, Z.-C.; Tang, Y.-R.; Wang, H.-X.; Liang, Y.-Y. Chem. Sci. 2022, 13, 11260. |
| [8] | Poirier, M.; Pouget, J. P.; Thompson, J. A.; Hoffman, B. M. Phys. Rev. B 1995, 51, 14861. |
| [9] | Zhong, H.-X.; Wang, M.-C.; Ghorbani-Asl, M.; Zhang, J.-C.; Ly, K. H.; Liao, Z.-Q.; Chen, G.-B.; Wei, Y.-D.; Biswal, B. P.; Zschech, E.; Weidinger, I. M.; Krasheninnikov, A. V.; Dong, R.-H.; Feng, X.-L. J. Am. Chem. Soc. 2021, 143, 19992. |
| [10] | Zhong, H.-X.; Ly, K. H.; Wang, M.-C.; Krupskaya, Y.; Han, X.-C.; Zhang, J.-C.; Zhang, J.; Kataev, V.; Buchner, B.; Weidinger, I. M.; Kaskel, S.; Liu, P.; Chen, M.-W.; Dong, R.-H.; Feng, X.-L. Angew. Chem., Int. Ed. Engl. 2019, 58, 10677. |
| [11] | Liu, Z.-L.; Zhang, X.-J.; Zhang, H.; Jiang, H.; Zhao, X.-M.; Shi, L.; Zhu, X.-J.; Hao, X.-Q.; Song, M.-P. Chin. J. Org. Chem. 2020, 40, 2755. (in Chinese) |
| [11] | ( 刘子林, 张小洁, 张恒, 姜辉, 赵雪梅, 石林林, 朱新举, 郝新奇, 宋毛平, 有机化学, 2020, 40, 2755.) |
| [12] | Yu, Z.-F.; Wang, L.-Y.; Mu, X.-J.; Chen, C.-C.; Wu, Y.-Y.; Cao, J.; Tang, Y. Angew. Chem., Int. Ed. 2021, 60, 6294. |
| [13] | Boileau, N. T.; Cranston, R.; Mirka, B.; Melville, O. A.; Lessard, B. H. RSC Adv. 2019, 9, 21478. |
| [14] | Wu, Y.-J.; Lv, F.-H.; Kan, J.-L.; Guan, Q.; Xue, A.-Q.; Wang, Q.-B.; Li, Y.-A.; Dong, Y.-B. RSC Adv. 2020, 10, 25958. |
| [15] | Luo, T.-K.; Nash, G. T.; Xu, Z.-W.; Jiang, X.-M.; Liu, J.-Q.; Lin, W.-B. J. Am. Chem. Soc. 2021, 143, 13519. |
| [16] | Furuyama, T.; Sato, T.; Kobayashi, N. J. Am. Chem. Soc. 2015, 137, 13788. |
| [17] | Furuyama, T.; Ogura, Y.; Yoza, K.; Kobayashi, N. Angew. Chem., Int. Ed. 2012, 51, 11110. |
| [18] | Kudrevich, S.; Brasseur, N.; La Madeleine, C.; Gilbert, S.; Van Lier, J. E. J. Med. Chem. 1997, 40, 3897. |
| [19] | Zheng, W.; Zhao, Y.; Zhuang, W.-H.; Wu, J.-J.; Wang, F.-Z.; Li, C.-H.; Zuo, J.-L. Angew. Chem., Int. Ed. 2018, 57, 15384. |
| [20] | De la Torre, G.; Bottari, G.; Torres, T. Adv. Energy Mater. 2017, 7, 1601700. |
| [21] | Dubbert, J.; Hoing, A.; Riek, N.; Knauer, S. K.; Voskuhl, J. Chem. Commun. 2020, 56, 7653. |
| [22] | Lee, K. H.; Leem, D. S.; Castrucci, J. S.; Park, K. B.; Bulliard, X.; Kim, K. S.; Jin, Y.-W.; Lee, S.; Bender, T. P.; Park, S. Y. ACS Appl. Mater. Interfaces 2013, 5, 13089. |
| [23] | Chan, H.; Wong, H. L.; Ng, M.; Poon, C. T.; Yam, V. W. J. Am. Chem. Soc. 2017, 139, 7256. |
| [24] | Gotfredsen, H.; Holmstrom, T.; Munoz, A. V.; Storm, F. E.; Tortzen, C. G.; Kadziola, A.; Mikkelsen, K. V.; Hammerich, O.; Nielsen, M. B. Org. Lett. 2018, 20, 5821. |
| [25] | Moreno-Simoni, M.; Torres, T.; de la Torre, G. Chem. Sci. 2022, 13, 9249. |
| [26] | Nohr, R. S.; McCallum, C. M.; Schuchmann, H. P. J. Porphyrins Phthalocyanines 2010, 14, 271. |
| [27] | Claessens, C. G.; Torres, T. Tetrahedron Lett. 2000, 41, 6361. |
| [28] | Shimizu, S.; Miura, A.; Khene, S.; Nyokong, T.; Kobayashi, N. J. Am. Chem. Soc. 2011, 133, 17322. |
| [29] | Wang, Y.-M.; Mori, S.; Furuta, H.; Shimizu, S. Angew. Chem., Int. Ed. 2019, 58, 10975. |
| [30] | Fulford, M. V.; Lough, A. J.; Bender, T. P. Acta Crystallogr., Sect. B: Struct. Sci. 2012, 68, 636. |
| [31] | Mori, S.; Ogawa, N.; Tokunaga, E.; Tsuzuki, S.; Shibata, N. Dalton Trans. 2016, 45, 908. |
| [32] | Guilleme, J.; Gonzalez-Rodriguez, D.; Torres, T. Angew. Chem., Int. Ed. 2011, 50, 3506. |
| [33] | Swarts, P. J.; Conradie, J. Inorg. Chem. 2020, 59, 7444. |
| [34] | Morse, G. E.; Bender, T. P. Inorg. Chem. 2012, 51, 6460. |
| [35] | Gotfredsen, H.; Jevric, M.; Broman, S. L.; Petersen, A. U.; Nielsen, M. B. J. Org. Chem. 2016, 1, 1. |
| [36] | Bukuroshi, E.; Petersen, A. U.; Brol?s, L.; Bender, T. P.; Nielsen, M. B. Eur. J. Inorg. Chem. 2020, 36, 3481. |
| [37] | Ma, F.; Zhang, G.-J.; Wu, X.-M.; Qu, W.-X.; Sun, Z.; Li, X.-G.; Yin, X.-H. J. Phys. Chem. C 2022, 126, 13496. |
| [38] | Guilleme, J.; Martinez-Fernandez, L.; Corral, I.; Yanez, M.; Gonzalez-Rodriguez, D.; Torres, T. Org. Lett. 2015, 17, 4722. |
| [39] | Berna, B. B.; Platzer, B.; Wolf, M.; Lavarda, G.; Nardis, S.; Galloni, P.; Torres, T.; Guldi, D. M.; Paolesse, R. Chem 2020, 26, 13451. |
| [40] | Platzer, B.; Ghazal, B.; Mari?as, V.; Labella, J.; Martínez-Díaz, M. V.; Maksheed, S.; Guldi, D. M.; Torres, T. ChemPhotoChem 2022, e202200213. |
| [41] | Nakano, S.; Kage, Y.; Furuta, H.; Kobayashi, N.; Shimizu, S. Chem. - Eur. J. 2016, 22, 7706. |
| [42] | Fujishiro, R.; Sonoyama, H.; Ide, Y.; Fujimura, T.; Sasai, R.; Kaufman, N. E. M.; Zhou, Z.-H.; Vicente, M. G. H.; Ikeue, T. J. Porphyrins Phthalocyanines 2020, 24, 212. |
| [43] | González-Rodríguez, D.; Torres, T. Eur. J. Org. Chem. 2009, 2009, 1871. |
| [44] | Gonzalez-Rodriguez, D.; Martinez-Diaz, M. V.; Abel, J.; Perl, A.; Huskens, J.; Echegoyen, L.; Torres, T. Org. Lett. 2010, 12, 2970. |
| [45] | Guilleme, J.; Aragó, J.; Ortí, E.; Cavero, E.; Sierra, T.; Ortega, J.; Folcia, C. L.; Etxebarria, J.; Gonzá lez-Rodríguez, D.; Torres, T. J. Mater. Chem. C 2015, 3, 985. |
| [46] | Kobayashi, N.; Kondo, R.; Nakajima, S.; Osa, T. J. Am. Chem. Soc. 1990, 112, 9640. |
| [47] | Caballero, E.; Fernandez-Ariza, J.; Lynch, V. M.; Romero-Nieto, C.; Rodriguez-Morgade, M. S.; Sessler, J. L.; Guldi, D. M.; Torres, T. Angew. Chem., Int. Ed. 2012, 51, 11337. |
| [48] | Mayoral, M. J.; Guilleme, J.; Calbo, J.; Arago, J.; Aparicio, F.; Orti, E.; Torres, T.; Gonzalez-Rodriguez, D. J. Am. Chem. Soc. 2020, 142, 21017. |
| [49] | Guilleme, J.; Mayoral, M. J.; Calbo, J.; Arago, J.; Viruela, P. M.; Orti, E.; Torres, T.; Gonzalez-Rodriguez, D. Angew. Chem., Int. Ed. 2015, 54, 2543. |
| [50] | Skvortsov, I. A.; Nikitin, I. A.; Lazovskiy, D. A.; Stuzhin, P. A. Dyes Pigm. 2022, 202, 110282. |
| [51] | Tejerina, L.; Martinez-Diaz, M. V.; Torres, T. Org. Lett. 2019, 21, 2908. |
| [52] | Shimizu, S.; Nakano, S.; Hosoya, T.; Kobayashi, N. Chem. Commun. 2011, 47, 316. |
| [53] | Stork, J. R.; Potucek, R. J.; Durfee, W. S.; Noll, B. C. Tetrahedron Lett. 1999, 40, 8055. |
| [54] | Wang, Y.-M.; Uchihara, K.; Mori, S.; Furuta, H.; Shimizu, S. Org. Lett. 2019, 21, 3103. |
| [55] | Xu, H.; Jiang, X.-J.; Chan, E. Y.; Fong, W. P.; Ng, D. K. Org. Biomol. Chem. 2007, 5, 3987. |
| [56] | Kuninobu, K.; Tsutomu, I.; Makoto, H.; Yoichi, U.; Takaji, F.; Kimio, I. Bull. Chem. Soc. Jpn. 1996, 69, 2559. |
| [57] | Paton, A. S.; Lough, A. J.; Bender, T. P. CrystEngComm 2011, 13, 3653. |
| [58] | Camerel, F.; Ulrich, G.; Retailleau, P.; Ziessel, R. Angew. Chem., Int. Ed. 2008, 47, 8876. |
| [59] | Rodriguez-Morgade, M. S.; Claessens, C. G.; Medina, A.; Gonzalez-Rodriguez, D.; Gutierrez-Puebla, E.; Monge, A.; Alkorta, I.; Elguero, J.; Torres, T. Chem.-Eur. J. 2008, 14, 1342. |
| [60] | Morse, G. E.; Castrucci, J. S.; Helander, M. G.; Lu, Z. H.; Bender, T. P. ACS Appl. Mater. Inter. 2011, 3, 3538. |
| [61] | Gonzalez-Rodriguez, D.; Torres, T.; Guldi, D. M.; Rivera, J.; Herranz, M. A.; Echegoyen, L. J. Am. Chem. Soc. 2004, 126, 6301. |
| [62] | Mutolo, K. L.; Mayo, E. I.; Rand, B. P.; Forrest, S. R.; Thompson, M. E. J. Am. Chem. Soc. 2006, 128, 8108. |
| [63] | Beaumont, N.; Cho, S. W.; Sullivan, P.; Newby, D.; Smith, K. E.; Jones, T. S. Adv. Funct. Mater. 2012, 22, 561. |
| [64] | Sullivan, P.; Duraud, A.; Hancox, l.; Beaumont, N.; Mirri, G.; Tucker, J. H. R.; Hatton, R. A.; Shipman, M.; Jones, T. S. Adv. Energy Mater. 2011, 1, 352. |
| [65] | Cnops, K.; Rand, B. P.; Cheyns, D.; Verreet, B.; Empl, M. A.; Heremans, P. Nat. Commun. 2014, 5, 3406. |
| [66] | Duan, C.-H.; Zango, G.; Garcia Iglesias, M.; Colberts, F. J.; Wienk, M. M.; Martinez-Diaz, M. V.; Janssen, R. A.; Torres, T. Angew. Chem., Int. Ed. 2017, 56, 148. |
| [67] | Hang, H.; Zhang, Z.-J.; Wu, X.-F.; Chen, Y.-H.; Li, H.; Wang, W.-J.; Tong, H.; Wang, L.-L. J. Mater. Chem. C 2018, 6, 7141. |
| [68] | Hang, H.; Wu, X.-F.; Xu, Q.; Chen, Y.-H.; Li, H.; Wang, W.-J.; Tong, H.; Wang, L.-L. Dyes Pigm. 2019, 160, 243. |
| [69] | Huang, T.-D.; Chen, H.; Feng, J.-J.; Zhang, A.-D.; Jiang, W.; He, F.; Wang, Z.-H. ACS Mater. Lett. 2019, 1, 404. |
| [70] | Huang, X.-S; Hu, M.; Zhao, X.-H.; Li, C.; Yuan, Z.-Y.; Liu, X.; Cai, C.-S.; Zhang, Y.-D.; Hu, Y.; Chen, Y.-W. Org. Lett. 2019, 21, 3382. |
| [71] | Jiang, D.-F.; Pan, Y.-F.; Yao, H.-Y.; Sun, J.-M.; Xiong, W.-W.; Li, L.-L.; Zheng, F.-F.; Sun, S.-S.; Zhu, J.-J. Anal. Chem. 2022, 94, 9074. |
| [72] | Yao, H.-Y.; Jiang, D.-F.; Dong, G.-Q.; Sun, J.-M.; Sun, S.-S.; Li, L.-L.; Zheng, F.-F.; Xiong, W.-W. Analyst 2021, 146, 5115. |
| [73] | Winckel, E.; Mascaraque, M.; Zamarrón, A.; Juarranz de la Fuente, á.; Torres, T.; Escosura, A. Adv. Funct. Mater. 2018, 28, 1705938. |
| [74] | Demuth, J.; Gallego, L.; Kozlikova, M.; Machacek, M.; Kucera, R.; Torres, T.; Martinez-Diaz, M. V.; Novakova, V. J. Med. Chem. 2021, 64, 17436. |
| [75] | Casellas, N. M.; Dai, G.; Xue, E. Y.; Fonseca, A.; Ng, D. K. P.; Garcia-Iglesias, M.; Torres, T. Chem. Commun. 2022, 58, 669. |
| [76] | Zhou, S.-T.; Lv, X.-J.; Li, M.-H.; Gao, Z.-J.; Tu, S.-N.; Qiao, S.-S.; Mo, M.-J.; Tang. X.; Wang, Y.-M.; Sun, S.-S. Molecules 2023, 28, 725. |
| [77] | Bernhard, Y.; Winckler, P.; Chassagnon, R.; Richard, P.; Gigot, E.; Perrier-Cornet, J. M.; Decreau, R. A. Chem. Commun. 2014, 50, 13975. |
| [78] | Roy, I.; Shetty, D.; Hota, R.; Baek, K.; Kim, J.; Kim, C.; Kappert, S.; Kim, K. Angew. Chem., Int. Ed. Engl. 2015, 54, 15152. |
| [79] | Ros-Lis, J. V.; Martinez-Manez, R.; Soto, J. Chem. Commun. 2005, 42, 5260. |
| [80] | Li, Y.; Xu, S.; Li, X.; Chen, K.-C.; Tian, H. Chem. Lett. 2007, 36, 664. |
| [81] | Arockiam, J. B.; Park, J. S. Spectrochim. Acta, Part A 2019, 207, 112. |
/
| 〈 |
|
〉 |
