Expanding the Porphycene Core: Modification and Metalation

Porphycenes, the first structural isomer of porphyrin, display unique chemical and photophysical properties. In this Account, we detail our group’s individual and collaborative efforts in elucidating further the chemical properties of porphycene. Particular emphasis will be placed on recent efforts devoted to expanding the porphycene core.

1 Introduction

2 Exploring the Chemistry of Porphycene

3 Synthesis and Metalation of an Expanded Porphycene

4 Conclusion

Key words

porphyrinoid - expanded porphycenes - coordination chemistry - porphycene materials - porphycene therapeutics - electronic communication - porphycenes - macrocycles - metal complexes - expanded porphyrins - hetero-annulenes

Full Text

References

References and Notes
1 Porphyrins and Metalloporphyrins . Smith KM. Elsevier; Amsterdam: 1976
2 Franck B, Nonn A. Angew. Chem., Int. Ed. Engl. 1995; 34: 1795
3 Tetrapyrroles: Birth, Life, and Death . Warren MJ, Smith AG. Springer; New York: 2009
4 Barona-Castano JC, Carmona-Vargas CC, Brocksom TJ, de Oliveira KT. Molecules 2016; 21: 310
5 Brothers PJ, Collman JP. Acc. Chem. Res. 1986; 19: 209
6 Auwarter W, Ecija D, Klapenberger F, Barth JV. Nat. Chem. 2015; 7: 105
7 Mamardashvili GM, Mamardashvili NZ, Koifman OI. Russ. Chem. Rev. 2005; 74: 765

8a Brenner W, Malig J, Costa RD, Guldi DM, Jux N. Adv. Mater. 2012; 25: 2314
8b Costa RD, Malig J, Brenner W, Jux N, Guldi DM. Adv. Mater. 2013; 25: 2600

9 Braslavsky SE, Muller M, Martire DO, Porting S, Bertolotti SG. J. Photochem. Photobiol., B 1997; 40: 191
10 Masiera N, Bojarska A, Gawryszewska I, Sadowy E, Hryniewicz W, Waluk J. J. Photochem. Photobiol., B 2017; 174: 84
11 Zhou Z, Shen Z. J. Mat. Chem. C 2015; 14: 3239
12 During the preparation of this manuscript an elegant demonstration of the utility of so-called functional building blocks was published by Professors Kim and Wu, see: Rana A, Hong Y, Gopalakrischna TY, Phan H, Herng TS, Yadav P, Ding J, Kim D, Wu J. Angew. Chem. Int. Ed. 2018; 57: 12534
13 Sanchez-Garcia D, Sessler JL. Chem. Soc. Rev. 2008; 37: 215
14 Anguera G, Sanchez-Garcia D. Chem. Rev. 2017; 117: 2481
15 Waluk J. Chem. Rev. 2017; 117: 2447
16 Malsch K, Hohlneicher G. J. Phys. Chem. A 1997; 101: 8409

17a Webb JL. A, Threlkeld RR. J. Org. Chem. 1953; 18: 1406
17b Webb JL. A. J. Org. Chem. 1953; 18: 1413

18 Grigg R, Johnson AW, Wasley JW. F. J. Chem. Soc. 1963; 359
19 Bauer VJ, Clive DL. J, Dolphin D, Paine JB. III, Harris FL, King MM, Loder J, Wang S.-WC, Woodward RB. J. Am. Chem. Soc. 1983; 105: 6429
20 Vogel E, Köcher M, Schmickler H, Lex J. Angew. Chem., Int. Ed. Engl. 1986; 25: 257
21 Vogel E, Balci M, Pramod K, Koch P, Lex J, Ermer O. Angew. Chem., Int. Ed. Engl. 1987; 26: 928
22 Sessler JL, Brucker EA, Lynch V, Choe M, Sorey S, Vogel E. Chem. Eur. J. 1996; 2: 1527
23 Vogel E, Broring M, Scholz P, Deponte R, Lex J, Schmickler H, Schaffner K, Braslavsky S, Muller M, Porting S, Weghorn SJ, Fowler CL, Sessler JL. Angew. Chem., Int. Ed. Engl. 1997; 36: 1651
24 Sessler JL, Fowler CJ, Gebauer A, Hegar A, Scholz P, Lex J, Vogel E. Chem. Eur. J. 2002; 8: 3485
25 Sargent AL, Hawkins IC, Allen WE, Liu H, Sessler JL, Fowler CJ. Chem. Eur. J. 2003; 9: 3065
26 Cuesta L, Karnas E, Lynch VM, Chen P, Shen J, Kadish KM, Ohkubo K, Fukuzumi S, Sessler JL. J. Am. Chem. Soc. 2009; 131: 13538
27 Roznyatovskiy V, Lynch V, Sessler JL. Org. Lett. 2010; 12: 4424
28 Vargas-Zuniga GI, Roznyatovskiy VV, Nepomnyaschii A, Lynch VM, Sessler JL. J. Porphyrins Phthalocyanines 2012; 16: 479
29 Jasat A, Dolphin D. Chem. Rev. 1997; 97: 2267
30 Sessler JL, Seidel D. Angew. Chem. Int. Ed. 2003; 42: 5134
31 Sessler JL, Tomat E. Acc. Chem. Res. 2007; 40: 371
32 Osuka A, Saito S. Chem. Commun. 2011; 15: 4330
33 Roznyatovskiy VV, Lee C.-H, Sessler JL. Chem. Soc. Rev. 2013; 5: 1921
34 Vargas-Zuniga GI, Sessler JL. Anion and Cation Complexes of Expanded Porphyrins . In Advances in Inorganic Chemistry: Supramolecular Chemistry . van Eldik R, Puchta R. Elsevier; Amsterdam: 2018
35 Bernard C, Gisselbrecht JP, Gross M, Jux N, Vogel E. J. Electroanal. Chem. 1995; 381: 159
36 Martire DO, Russell S, Dietrich H.-J, Cobos CJ, Braslavsky SE. J. Porphyrins Phthalocyanines 2012; 16: 499
37 Jux N, Koch P, Schmickler H, Lex J, Vogel E. Angew. Chem., Int. Ed. Engl. 1990; 29: 1385
38 Rana A, Lee S, Kim D, Panda PK. Chem. Eur. J. 2015; 21: 12129
39 Miller DC, Johnson MR, Ibers JA. J. Org. Chem. 1994; 59: 2877
40 Setsune J, Toda M, Yoshida T. Chem. Commun. 2008; 1425
41 Setsune J, Toda M, Yoshida T, Imamura K, Watanabe K. Chem. Eur. J. 2015; 21: 12715
42 Anguera G, Cha W.-Y, Moore MD, Brewster JT. II, Zhao MY, Lynch VD, Kim D, Sessler JL. Angew. Chem. Int. Ed. 2018; 57: 2575
43 Will S, Rahbar A, Schmickler H, Lex J, Vogel E. Angew. Chem., Int. Ed. Engl. 1990; 29: 1390
44 Commercial basic alumina for column chromatography is treated with base to adjust the pH of a 10% slurry (w/v in water) to pH ca. 10.