Exploring Porphyrins, Phthalocyanines and Corroles as Photocatalysts for Organic Transformations

Ashmita Jain; Iti Gupta

doi:10.1055/s-0040-1720126

SynOpen, Inhaltsverzeichnis

CC BY 4.0 · SynOpen 2024; 08(03): 153-168
DOI: 10.1055/s-0040-1720126

graphical review

Exploring Porphyrins, Phthalocyanines and Corroles as Photocatalysts for Organic Transformations

Ashmita Jain

,

Iti Gupta∗

Abstract

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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.

Key words

photocatalysis - photoredox catalysis - porphyrins - phthalocyanines - corroles

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Referenzen

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