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A flexible expanded heterocorrole: Tellura[22]porphyrin(6.1.1.0)

Sandra Hojniak-Thyssen

Department of Chemistry, University of Wrocław, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland

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Michał Szczepaniak

Department of Chemistry, University of Wrocław, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland

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Lechosław Latos-Grażyński

Department of Chemistry, University of Wrocław, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland

SPP full member in good standing.

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, and

Ewa Pacholska-Dudziak

Department of Chemistry, University of Wrocław, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland

E-mail Address: ewa.dudziak@chem.uni.wroc.pl

Corresponding author, tel.: +48-71-375-7016.

SPP full member in good standing.

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https://doi.org/10.1142/S1088424619501621Cited by:0 (Source: Crossref)

Abstract

An expanded heterocorrole, meso-tetraaryl-tellura[22]porphyrin(6.1.1.0), containing a bipyrrole moiety and a six-carbon long link, has been synthesized. The reaction path proceeds through a controlled acid-promoted extrusion of one tellurium atom from meso-aryl-26,28-ditellurasapphyrin, leading to a structure where one tellurophene ring of the substrate is replaced by a bridging acyclic four-carbon unit. This aromatic porphyrin-annulene hybrid is conformationally flexible in solution, on account of the C₄ unit adopting two different configurations: trans–cis–trans or all-trans. Studies of the dynamic behavior of tellura[22]porphyrin(6.1.1.0) in solution were performed by means of ¹H and ¹²⁵Te NMR spectroscopy. The X-ray structure of the all-trans form with trapezoid macrocyclic skeleton is also presented.

This paper is part of the 2019 Women in Porphyrin Science special issue.

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References

1. Sondheimer F, Wolovsky R and Amiel Y . J. Am. Chem. Soc. 1962; 84: 274–284. Crossref, Web of Science, Google Scholar
2. Vogel E . Pure Appl. Chem. 1993; 65: 143–152. Crossref, Web of Science, Google Scholar
3. Anguera G and Sanchez-Garcia D . Chem. Rev. 2017; 117: 2481–2516. Crossref, Web of Science, Google Scholar
4. Vogel E, Kocher M, Schmickler H and Lex J . Angew. Chem., Int. Ed. Engl. 1986; 25: 257–259. Crossref, Web of Science, Google Scholar
5. König H, Eickmeier C, Möller M, Rodewald U and Franck B . Angew. Chem., Int. Ed. Engl. 1990; 29: 1393–1395. Crossref, Web of Science, Google Scholar
6. Vogel E, Jux N, Rodriguezval E, Lex J and Schmickler H . Angew. Chem,. Int. Ed. Engl. 1990; 29: 1387–1390. Crossref, Web of Science, Google Scholar
7. Vogel E, Rohrig P, Sicken M, Knipp B, Herrmann A, Pohl M, Schmickler H and Lex J . Angew. Chem., Int. Ed. Engl. 1989; 28: 1651–1655. Crossref, Web of Science, Google Scholar
8. Vogel E, Jux N, Dörr J, Pelster T, Berg T, Böhm HS, Behrens F, Lex J, Bremm D and Hohlneicher G . Angew. Chem., Int. Ed. 2000; 39: 1101–1105. Crossref, Web of Science, Google Scholar
9. Waluk J and Michl J . J. Org. Chem. 1991; 56: 2729–2735. Crossref, Web of Science, Google Scholar
10. Jusélius J and Sundholm D . Phys. Chem. Chem. Phys. 2000; 2: 2145–2151. Crossref, Web of Science, Google Scholar
11. Cyrański MK, Krygowski TM, Wisiorowski M, Hommes NJRV and Schleyer PV . Angew. Chem., Int. Ed. 1998; 37: 177–180. Crossref, Web of Science, Google Scholar
12. Aihara J, Nakagami Y, Sekine R and Makino M . J. Phys. Chem. A 2012; 116: 11718–11730. Crossref, Web of Science, Google Scholar
13. Bohusch M, Flitsch W and Kneip HG . Liebigs Ann. 1991; 67–70. Crossref, Google Scholar
14. Chang CK, Wu WS, Chern SS and Peng SM . Angew. Chem., Int. Ed. Engl. 1992; 31: 70–72. Crossref, Web of Science, Google Scholar
15. Pacholska E, Latos-Grażyński L and Ciunik Z . Chem. — Eur. J. 2002; 8: 5403–5406. Crossref, Web of Science, Google Scholar
16. Pacholska-Dudziak E, Szterenberg L and Latos-Grażyński L . Chem. — Eur. J. 2011; 17: 3500–3511. Crossref, Web of Science, Google Scholar
17. Lash TD, Jones SA and Ferrence GM . J. Am. Chem. Soc. 2010; 132: 12786–12787. Crossref, Web of Science, Google Scholar
18. Pacholska-Dudziak E, Skonieczny J, Pawlicki M, Szterenberg L, Ciunik Z and Latos-Grażyński L . J. Am. Chem. Soc. 2008; 130: 6182–6195. Crossref, Web of Science, Google Scholar
19. McQuilkin RM, Metcalf BW and Sondheimer F . J. Chem. Soc. D 1971; 338–339. Crossref, Google Scholar
20. Wannere CS, Sattelmeyer KW, Schaefer HF and Schleyer PV . Angew. Chem., Int. Ed. 2004; 43: 4200–4206. Crossref, Web of Science, Google Scholar
21. Chmielewski PJ, Latos-Grażyński L and Rachlewicz K . Chem. — Eur. J. 1995; 1: 68–73. Crossref, Web of Science, Google Scholar
22. Sessler JL and Davis JM . Acc. Chem. Res. 2001; 34: 989–997. Crossref, Web of Science, Google Scholar
23. Setsune J . Chem. Rev. 2017; 117: 3044–3101. Crossref, Web of Science, Google Scholar
24. Pacholska-Dudziak E, Latos-Grażyński L and Białońska A . Chem. — Eur. J. 2019; 25: 10088–10097. Crossref, Web of Science, Google Scholar
25. Gosmann M, Vogt A and Franck B . Liebigs Ann. 1990; 163–168. Crossref, Google Scholar
26. Xu LL, Ferrence GM and Lash TD . Org. Lett. 2006; 8: 5113–5116. Crossref, Web of Science, Google Scholar
27. Hong JH, Aslam AS, Ko MS, Choi J, Lee Y and Cho DG . Chem. — Eur. J. 2018; 24: 10054–10058. Crossref, Web of Science, Google Scholar
28. Beckmann S, Wessel T, Franck B, Hönle W, Borrmann H and Vonschnering HG . Angew. Chem., Int. Ed. Engl. 1990; 29: 1395–1397. Crossref, Web of Science, Google Scholar
29. Märkl G, Sauer H, Kreitmeier P, Burgemeister T, Kastner F, Adolin G, Nöth H and Polborn K . Angew. Chem., Int. Ed. Engl. 1994; 33: 1151–1153. Crossref, Web of Science, Google Scholar
30. Märkl G, Hafner M, Kreitmeier P, Burgemeister T, Kastner F, Porsch M and Daub J . Tetrahedron 1996; 52: 1981–1996. Crossref, Web of Science, Google Scholar
31. Märkl G, Ehrl R, Kreitmeier P and Burgemeister T . Helv. Chim. Acta 1998; 81: 93–108. Crossref, Web of Science, Google Scholar
32. Hu ZY and Cava MP . Tetrahedron Lett. 1994; 35: 3493–3496. Crossref, Web of Science, Google Scholar
33. Liu H, Qin YK, Xu W and Zhu D . Asian J. Org. Chem. 2014; 3: 1302–1307. Crossref, Web of Science, Google Scholar
34. Makhal K, Arora S, Kaur P, Goswami D and Singh K . J. Mater. Chem. C 2016; 4: 9445–9453. Crossref, Google Scholar
35. Singh K, Virk TS, Zhang J, Xu W and Zhu DB . Chem. Commun. 2012; 48: 121–123. Crossref, Web of Science, Google Scholar
36. Zhao TY, Wei ZM, Song YB, Xu W, Hu WP and Zhu DB . J. Mater. Chem. 2007; 17: 4377–4381. Crossref, Google Scholar
37. Xi HX, Wei ZM, Xu W, Bo ZS, Hu WP and Zhu DB . Chem. Phys. Lett. 2009; 484: 41–43. Crossref, Web of Science, Google Scholar
38. Virk TS, Kaur P and Singh K . Spectrochim. Acta A 2018; 205: 534–539. Crossref, Web of Science, Google Scholar
39. Sathyamoorthy B, Axelrod A, Farwell V, Bennett SM, Calitree BD, Benedict JB, Sukumaran DK and Detty MR . Organometallics 2010; 9: 3431–3441. Crossref, Web of Science, Google Scholar
40. Bröring M, Dietrich HJ, Dörr J, Hohlneicher G, Lex J, Jux N, Pütz C, Roeb M, Schmickler H and Vogel E . Angew. Chem. Int. Ed. 2000; 39: 1105–1108. Crossref, Web of Science, Google Scholar
41. Stępień M, Szyszko B and Latos-Grażyński L . J. Am. Chem. Soc. 2010; 132: 3140–3152. Crossref, Web of Science, Google Scholar
42. Pacholska-Dudziak E, Hojniak-Thyssen S and Latos-Grażyński L . Chem. Eur. J. 2019; 25: 11859–11863. Crossref, Web of Science, Google Scholar
43. Pacholska-Dudziak E, Szczepaniak M, Ksi ążek A and Latos-Grażyński L. Angew. Chem. Int. Ed. 2013; 52: 8898–8903. Crossref, Web of Science, Google Scholar