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Deep-cavity subporphyrazines with extended $π$ $π$ -perimeters

Institute for Chemistry and CINSaT — Center for Interdisciplinary Nanostructure Science and Technology, University of Kassel, Heinrich-Plett-Str. 40, D-34132 Kassel, Germany

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Patricia Löser

Institute for Chemistry and CINSaT — Center for Interdisciplinary Nanostructure Science and Technology, University of Kassel, Heinrich-Plett-Str. 40, D-34132 Kassel, Germany

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Andreas Winzenburg

Institute for Chemistry and CINSaT — Center for Interdisciplinary Nanostructure Science and Technology, University of Kassel, Heinrich-Plett-Str. 40, D-34132 Kassel, Germany

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, and

Rüdiger Faust

Institute for Chemistry and CINSaT — Center for Interdisciplinary Nanostructure Science and Technology, University of Kassel, Heinrich-Plett-Str. 40, D-34132 Kassel, Germany

E-mail Address: r.faust@uni-kassel.de

Corresponding author; fax: +49 561-804-4752, tel: +49 561-804-4750

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https://doi.org/10.1142/S1088424616501078Cited by:9 (Source: Crossref)

Abstract

Unprecedentedly large subporphyrazines (SubPz) with dibenzoquinoxalino-fusion and peripheral phenyl substitution were prepared by the cyclization of perfluorated or non-fluorous polyphenyl-substituted quinoxaline dinitriles and characterized by spectroscopic techniques. The compounds suitability to act as photosensitizers was explored by wavelength-specific induction of singlet oxygen luminescence and was shown to be excellent. Determination of ¹O₂-quantum yields suggests that fluorine substitution enhances the photosensitization efficiencies of the SubPz. On the other hand, cyclic voltammetry reveals an increase of irreversible reductive processes in case of the fluorinated SubPz.

Dedicated to Professor Tomás Torres on the occasion of his 65th birthday

Keywords:

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References

1. Meller A and Ossko A. Monatsh. Chem. 1972; 103: 150–155. Crossref, Web of Science, Google Scholar
2. Torres T. Angew. Chem., Int. Ed. 2006; 45: 2834–2837. Crossref, Web of Science, Google Scholar
3. Rodríguez-Morgade MS, Esperanza S, Torres T and Barberá J. Chem. — Eur. J. 2005; 11: 354–360. Crossref, Web of Science, Google Scholar
4. Claessens CG, González-Rodríguez D and Torres T. Chem. Rev. 2002; 102: 835–854. Crossref, Web of Science, Google Scholar
5. Higashino T, Rodríguez-Morgade MS, Osuka A and Torres T. Chem. — Eur. J. 2013; 19: 10353–10359. Crossref, Web of Science, Google Scholar
6. The term “subphthalocyanine” is used to denote compounds with tribenzo-fusion to the subtriazaporphyrin core. For unfused triazasubporphyrin and for compounds with fusion patterns other than benzo, the term “subporphyrazine” is used. Google Scholar
7. Martín G, Rojo G, Agulló-López F, Ferro VR, García de la Vega JM, Martínez-Díaz MV, Torres T, Ledoux I and Zyss J. J. Phys. Chem. B 2002; 106: 13139–13145. Crossref, Web of Science, Google Scholar
8. Claessens CG, González-Rodríguez D, Torres T, Martín G, Agulló-López F, Ledoux I, Zyss J, Ferro VR and García de la Vega JM. J. Phys. Chem. B 2005; 109: 3800–3806. Crossref, Web of Science, Google Scholar
9. González-Rodríguez D, Torres T, Guldi DM, Rivera J, Herranz MÁ and Echegoyen L. J. Am. Chem. Soc. 2004; 126: 6301–6313. Crossref, Web of Science, Google Scholar
10. González-Rodríguez D, Claessens CG, Torres T, Liu S, Echegoyen L, Vila N and Nonell S. Chem. — Eur. J. 2005; 11: 3881–3893. Crossref, Web of Science, Google Scholar
11. González-Rodríguez D, Torres T, Olmstead MM, Rivera J, Herranz MÁ, Echegoyen L, Castellanos CA and Guldi DM. J. Am. Chem. Soc. 2006; 128: 10680–10681. Crossref, Web of Science, Google Scholar
12. González-Rodríguez D, Carbonell E, Guldi DM and Torres T. Angew. Chem., Int. Ed. 2009; 48: 8032–8036. Crossref, Web of Science, Google Scholar
13. Wang Y, Gu D and Gan F. Phys. Status Solidi A 2001; 186: 71–77. Crossref, Google Scholar
14. Xu S, Chen K and Tian H. J. Mater. Chem. 2005; 15: 2676–2680. Crossref, Web of Science, Google Scholar
15. Palomares E, Martínez-Díaz MV, Torres T and Coronado E. Adv. Funct. Mater. 2006; 16: 1166–1170. Crossref, Web of Science, Google Scholar
16. Rahman GMA, Lüders D, Rodríguez-Morgade MS, Caballero E, Torres T and Guldi DM. ChemSusChem 2009; 2: 330–335. Crossref, Web of Science, Google Scholar
17. Berliner LJ, Görner H and Schuchmann H-P. J. Porphyrins Phthalocyanines 2011; 15: 118–121. Link, Web of Science, Google Scholar
18. Kobayashi N, Kondo R, Nakajima S and Osa T. J. Am. Chem. Soc. 1990; 112: 9640–9641. Crossref, Web of Science, Google Scholar
19. Sharman WM and van Lier JE. J. Porphyrins Phthalocyanines 2005; 9: 651–658. Link, Web of Science, Google Scholar
20. Matlaba P and Nyokong T. Polyhedron 2002; 21: 2463–2472. Crossref, Web of Science, Google Scholar
21. Tempesti TC and Baumgartner MT. J. Porphyrins Phthalocyanines 2015; 19: 1088–1094. Link, Web of Science, Google Scholar
22. González-Rodríguez D and Torres T. Eur. J. Org. Chem. 2009; 2009: 1871–1879. Crossref, Web of Science, Google Scholar
23. Sharman WM and Van Lier JE. In The Porphyrin Handbook, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: Amsterdam, 2003; pp. 1–60. Crossref, Google Scholar
24. Ferro VR, García de la Vega JM, Claessens CG, Poveda LA and GonzÁlez-Jonte RH. J. Porphyrins Phthalocyanines 2001; 5: 491–499. Link, Web of Science, Google Scholar
25. Morse GE, Paton AS, Lough A and Bender TP. Dalton Trans. 2010; 39: 3915–3922. Crossref, Web of Science, Google Scholar
26. Paton AS, Morse GE, Lough AJ and Bender TP. Cryst. Growth Des. 2013; 13: 5368–5374. Crossref, Web of Science, Google Scholar
27. Camerel F, Ulrich G, Retailleau P and Ziessel R. Angew. Chem., Int. Ed. 2008; 47: 8876–8880. Crossref, Web of Science, Google Scholar
28. González-Rodríguez D, Carbonell E, Rojas GdM, Castellanos CA, Guldi DM and Torres T. J. Am. Chem. Soc. 2010; 132: 16488–16500. Crossref, Web of Science, Google Scholar
29. Löser P, Winzenburg A and Faust R. Chem. Commun. 2013; 49: 9413–9415. Crossref, Web of Science, Google Scholar
30. Seikel E. PhD Thesis; University of Marburg: Marburg, 2012. Google Scholar
31. Enokida T and Suda Y. Organic electroluminescent device material containing organic boron compound and device using it, Patent JP 07102251 (Toyo Ink Mfg Co, Japan), 1993. Google Scholar
32. Enoki O. Photoelectric conversion film for solid-state imaging element and electronic device, Patent JP 2016009722 (Sony Corp., Japan), 2016. Google Scholar
33. Tempesti TC and Durantini EN. Proc. Int. Electr. Conf. Synth. Org. Chem. 2007: a025/021–a025/028. Google Scholar
34. Solntsev PV, Spurgin KL, Sabin JR, Heikal AA and Nemykin VN. Inorg. Chem. 2012; 51: 6537–6547. Crossref, Web of Science, Google Scholar
35. Armarego WLF and Chai CLL. Purification of Laboratory Chemicals, 7. Ed., Butterworth-Heinemann: Boston, 2013. Google Scholar
36. Wilkinson F, Helman WP and Ross AB. J. Phys. Chem. Ref. Data 1993; 22: 113–262. Crossref, Web of Science, Google Scholar
37. Claessens CG, González-Rodríguez D, Rodríguez-Morgade MS, Medina A and Torres T. Chem. Rev. 2013; 114: 2192–2277. Crossref, Web of Science, Google Scholar