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CC BY 4.0 · SynOpen 2024; 08(03): 153-168
DOI: 10.1055/s-0040-1720126
DOI: 10.1055/s-0040-1720126
graphical review
Exploring Porphyrins, Phthalocyanines and Corroles as Photocatalysts for Organic Transformations
I.G. thanks the Council of Scientific & Industrial Research (CSIR), Government of India (Grant No. 01/3132/23/EMR-II) and the Indian Institute of Technology Gandhinagar (IIT Gandhinagar) for financial support. A.J. thanks IIT Gandhinagar for a fellowship.
Abstract
In recent years, macrocycles have emerged as efficient and sustainable photosensitizers for the catalysis of organic transformations. This graphical review provides a concise overview of photocatalysis and photoredox catalysis utilizing three common macrocycles: porphyrins, phthalocyanines and corroles. They exhibit strong absorption in the visible region and can be easily oxidized or reduced, making them good candidates for photocatalysis.
Publication History
Received: 27 March 2024
Accepted after revision: 26 June 2024
Article published online:
13 August 2024
© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References
- 1 Majek M, Wangelin AJ. Acc. Chem. Res. 2016; 49: 2316
- 2 Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
- 3 Pitre SP, McTiernan CD, Scaiano JC. Acc. Chem. Res. 2016; 49: 1320
- 4a Crisenza GE. M, Melchiorre P. Nat. Commun. 2020; 11: 803
- 4b Takeda H, Ishitani O. Coord. Chem. Rev. 2010; 254: 346
- 4c Gratzel M. Acc. Chem. Res. 1981; 14: 376
- 4d Kalyanasundaram K, Gratzel M. Chem. Rev. 1998; 77: 347
- 5a Rueping M, Zhu S, Koenig RM. Chem. Commun. 2011; 47: 8679
- 5b Nguyen JD, Tucker JW, Konieczynska MD, Stephenson CR. J. J. Am. Chem. Soc. 2011; 133: 4160
- 5c Ischay MA, Anzovino ME, Du J, Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886
- 6a Millet A, Cesana PT, Sedillo K, Bird MJ, Schlau-Cohen GS, Doyle AG, MacMillan DW. C, Scholes GD. Acc. Chem. Res. 2022; 55: 1423
- 6b Chan AY, Perry IB, Bissonnette NB, Buksh BF, Edwards GA, Frye LI, Garry OL, Lavagnino MN, Li BX, Liang Y, Mao E, Millet A, Oakley JV, Reed NL, Sakai HA, Seath CP, MacMillan DW. C. Chem. Rev. 2022; 122: 1485
- 6c Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
- 7a Majek M, Filace F, von Wangelin AJ. Beilstein J. Org. Chem. 2014; 10: 981
- 7b Herbrik F, Camarero González P, Krstic M, Puglisi A, Benaglia M, Sanz MA, Rossi S. Appl. Sci. 2020; 10: 5596
- 8a Gross Z, Simkhovich L, Galili N. Chem. Commun. 1999; 599
- 8b Grodkowski J, Neta P, Fujita E, Mahammed A, Simkhovich L, Gross Z. J. Phys. Chem. A 2022; 106: 4772
- 8c Luobeznova I, Raizman M, Goldberg I, Gross Z. Inorg Chem. 2006; 45: 386
- 9a Sorokin AB. Chem. Rev. 2013; 113: 8152
- 9b Sorokin AB, Kudrik EV. Catal. Today 2011; 159: 37
- 9c Ji D, Lu X, He R. Appl. Catal., A 2000; 203: 329
- 10a Herreo C, Quaranta A, Ricoux R, Trehoux A, Mahammed A, Gross Z, Banse F, Mahy J.-P. Dalton Trans. 2016; 45: 706
- 10b Gross Z, Golubkov G, Simkhovich L. Angew. Chem. Int. Ed. 2000; 39: 4045
- 11 Janaagal A, Pandey V, Sabharwal S, Gupta I. J. Porphyrins Phthalocyanines 2021; 25: 571
- 12 Owens JW, Smith R, Robinson R, Robins M. Inorg. Chim. Acta 1998; 279: 226
- 13 Wasbotten JH, Conradie J, Ghosh A. J. Phys. Chem. B 2003; 107: 3613
- 14 Pandey V, Jain D, Pareek N, Gupta I. Inorg. Chim. Acta 2020; 502: 119339
- 15 Pandey V, Janaagal A, Jain A, Mori S, Gupta I. Dyes Pigm. 2023; 209: 110861
- 16 Hajimohammadi M, Safari N, Mofakham H, Shaabani A. Tetrahedron Lett. 2010; 51: 4061
- 17 Hajimohammadi M, Mofakham H, Safari N, Manesh AM. J. Porphyrins Phthalocyanines 2012; 16: 93
- 18 Malone J, Klaine S, Alcantar C, Bratcher F, Zhang R. New J. Chem. 2021; 45: 4977
- 19 Capaldo L, Ertl M, Fagnoni M, Knor G, Ravelli D. ACS Catal. 2020; 10: 9057
- 20 Shremzer ES, Polivanovskaia DA, Birin KP, Gorbunova YG, Tsivadze AY. Dyes Pigm. 2023; 210: 110935
- 21 Palivanovskaia DA, Abdulaeva IA, Birin KP, Gorbunova YG, Tsivadze AY. J. Catal. 2022; 413: 342
- 22 Yamashita K, Sugiura K. Tetrahedron Lett. 2019; 60: 151081
- 23 Zhang P, Yu C, Yin Y, Droste J, Klabunde S, Hansen MR, Mai Y. Chem. Eur. J. 2020; 69: 16497
- 24 Cheng Y, Zhang Z, Duan X, Zhang M. Dalton Trans. 2022; 51: 16517
- 25 Hong YH, Han JW, Jung J, Nakagawa T, Lee Y.-M, Nam W, Fukuzumi S. J. Am. Chem. Soc. 2019; 141: 9155
- 26 Jasinska KR, Wdowik T, Łuczak K, Wierzba AJ, Drapala O, Gryko D. ACS Org. Inorg. Au 2022; 2: 422
- 27 Wang HH, Shao H, Huang G, Fan J, To WP, Dang L, Liu Y, Che CM. Angew. Chem. Int. Ed. 2023; 62: e202303981
- 28 Yu XY, Su H, Zheng X, Liu WB, He Y, Fei NN, Qiao R, Ren YL, Niu CY. J. Mol. Struct. 2021; 1237: 130358
- 29 Jasinska KR, Konig B, Gryko D. Eur. J. Org. Chem. 2017; 2104
- 30 Castano JC. B, Carmona-Vargas CC, Brckson TJ, Oliveira KT. Molecules 2016; 21: 310
- 31 Fukuzumi S, Nam W. J. Porphyrins Phthalocyanines 2016; 20: 35
- 32 Jasinska K, Shan W, Zawada K, Kadish KM, Gryko D. J. Am. Chem. Soc. 2016; 138: 15451
- 33 Silva RC, Silva LO, Bartolomeu AD. A, Brocksom TJ, Oliveira KT. Beilstein J. Org. Chem. 2020; 16: 917
- 34 Souza AA. N, Silva NS, Muller AV, Polo AS, Brocksom TJ, Oliveira KT. J. Org. Chem. 2018; 83: 15077
- 35 Hajimohammadi M, Safari N, Mofakham H, Deyhimi F. Green Chem. 2011; 13: 991
- 36 Hajimohammadi M, Safari N. J. Porphyrins Phthalocyanines 2010; 14: 639
- 37 Gao X, Tong X, Liu R, Zhang Y. Catal. Sci. Technol. 2023; 13: 6132
- 38 Jasinska KR, Ciszewski LW, Gryko DT, Gryko D. J. Porphyrins Phthalocyanines 2016; 20: 76
- 39 Li BZ, Qian YY, Liu J, Chan KS. Organometallics 2014; 33: 7059
- 40 Janaagal A, Sanyam, Mondal A, Gupta I. J. Org. Chem. 2023; 88: 9424
- 41 Gao X, Tong X, Zhang Y, Xue S. iScience 2023; 7: 107203
- 42 Du YD, Zhou CY, To WP, Wang HX, Che CM. Chem. Sci. 2020; 11: 4680
- 43 Asghari S, Farahmand S, Razavizadeh JS, Ghiaci M. J. Photochem. Photobiol., A 2020; 392: 112412
- 44 Ozturmen BA, Akkol C, Saka ET, Biyiklioglu Z. Inorg. Chem. Commun. 2023; 158: 111647
- 45 Chauhan SM. S, Srinivas KA, Srivastava PK, Sahoo B. J. Porphyrins Phthalocyanines 2003; 7: 548
- 46 Yalazan H, Akkol C, Saka ET, Kantekin H. Appl. Organomet. Chem. 2023; 37: e6975
- 47 Katsurayama Y, Ikabata Y, Maeda H, Segi M, Nakai H, Furuyama T. Chem. Eur. J. 2023; 28: e202103223
- 48 Yalazan H, Tekintas K, Serdaroglu V, Saka ET, Kahriman N, Kantekin H. Inorg. Chem. Commun. 2020; 118: 107998
- 49 Saka ET, Tekintas K, Bekircan O, Biyiklioglu Z. Inorg. Chim. Acta 2023; 547: 121342
- 50 Saka ET, Cakmak U, Akkol C, Biyiklioglu Z. Polyhedron 2023; 243: 116522
- 51 Grundke C, Silva RC, Kitzmann WR, Heinze K, Oliveira KT, Opatz T. J. Org. Chem. 2022; 87: 5630
- 52 Liu L, Lin J, Pang M, Jin H, Yu X, Wang S. Org. Lett. 2022; 24: 1146
- 53 Yerien DE, Cooke MV, Vior MC. G, Vallejo SB, Postigo A. Org. Biomol. Chem. 2019; 17: 3741
- 54 Dickerson SD, Ayare PJ, Vannucci AK, Wiskur SL. J. Photochem. Photobiol., A 2022; 422: 113547
- 55 Fazli H, Akkol C, Osmanogullari SC, Bekircan O. J. Organomet. Chem. 2023; 983: 122553
- 56 Lancel M, Golisano T, Monnereau C, Gomez C, Port M, Amara Z. ACS Sustainable Chem. Eng. 2023; 11: 15674
- 57 Ishikawa Y, Kameyama T, Torimoto T, Maeda H, Segi M, Furuyama T. Chem. Commun. 2021; 57: 13594
- 58 Saka ET, Tekintas K. J. Mol. Struct. 2020; 1215: 128189
- 59 Chen J, Zhu C, Xu Y, Zhang P, Liang T. Curr. Org. Chem. 2018; 22: 485
- 60 Laliya OK, Lukyanets EA, Vorozhtsov GN. J. Porphyrins Phthalocyanines 1999; 3: 592
- 61 Lever AB. P. Adv. Inorg. Chem. Radiochem. 1965; 7: 27
- 62 Moons H, Loas A, Gorun SM, Doorslaer SV. Dalton Trans. 2014; 43: 14942
- 63 Marais E, Klein R, Antunes E, Nyokong T. J. Mol. Catal. A: Chem. 2007; 261: 36
- 64 Iliev V, Bilyarska VA. J. Mol. Catal. A: Chem. 1999; 137: 15
- 65 Ogunbayo TB, Nyokong T. J. Mol. Struct. 2010; 973: 96
- 66 Tau P, Nyokong T. J. Mol. Catal. A: Chem. 2007; 273: 149
- 67 Koohgard M, Sarvari MH. Org. Biomol. Chem. 2021; 19: 5905
- 68 Ding T, Aleman EA, Modarelli DA, Ziegler CJ. J. Phys. Chem. A 2005; 109: 7411
- 69 Mahammed A, Gross Z. Angew. Chem. Int. Ed. 2015; 54: 12547
- 70 Harel IA, Gross Z. Chem. Eur. J. 2009; 15: 8382
- 71 Aviv I, Gross Z. Chem. Commun. 2007; 20: 1987
- 72 Lemon CM. Pure Appl. Chem. 2020; 92: 1901
- 73 Gryko DT. Eur. J. Org. Chem. 2002; 1735
- 74 Natale CD, Gros CP, Paolesse R. Chem. Soc. Rev. 2022; 51: 1277
- 75 Orlowski R, Gryko D, Gryko DT. Chem. Rev. 2017; 117: 3102
- 76 Lemon CM, Maher AG, Mazzotti AR, Powers DC, Gonzalez MI, Nocera DG. Chem. Commun. 2020; 56: 5247
- 77 Reith LM, Stiftinger M, Monkowius U, Knor G, Schoefberger W. Inorg. Chem. 2011; 50: 6788
- 78 Zhan X, Kolanu S, Fite S, Chen QC, Lee W, Churchill DG, Gross Z. Photochem. Photobiol. Sci. 2020; 19: 996
- 79 Zhan X, Teplitzky P, Posner YD, Sundararajan M, Ullah Z, Chen QC, Shimon LJ. W, Saltsman I, Mahammed A, Kosa M, Baik MH, Churchill DG, Gross Z. Inorg. Chem. 2019; 58: 6184
- 80 Mahammed A, Chen K, Vestfrid J, Zhao J, Gross Z. Chem. Sci. 2019; 10: 7091
- 81 Zhan X, Yadav P, Posner YD, Fridman N, Sundararajan M, Ullah Z, Chen QC, Shimon LJ. W, Mahammed A, Churchill DG, Baik MH, Gross Z. Dalton Trans. 2019; 48: 12279