ArticlesNo Access

Synthesis, characterization and photochemical properties of metallo porphyrazines substituted with alkyl linked carbazole, benzoazepine and phenothiazine moieties

Remziye Olgaç

Department of Chemistry, Pamukkale University, Kınıklı/Denizli-Turkey, Turkey

Search for more papers by this author

Yasemin Baygu

Vocational School of Higher Education, Pamukkale University, Tavas/Denizli-Turkey, Turkey

Search for more papers by this author

Burak Yıldız

Department of Chemistry, Pamukkale University, Kınıklı/Denizli-Turkey, Turkey

Search for more papers by this author

Yaşar Gök

Department of Chemistry, Pamukkale University, Kınıklı/Denizli-Turkey, Turkey

E-mail Address: gyasar@pau.edu.tr

Correspondence to: Dr. Yaşar Gök, Department of Chemistry, Pamukkale University, Denizli 20017 Turkey. Tel.:+90 296 3567.

Search for more papers by this author

Baybars Köksoy

Department of Chemistry, Gebze Technical University, P.K. 141, 41400, Gebze/Kocaeli-Turkey, Turkey

Search for more papers by this author

, and

Mahmut Durmuş

Department of Chemistry, Gebze Technical University, P.K. 141, 41400, Gebze/Kocaeli-Turkey, Turkey

Search for more papers by this author

https://doi.org/10.1142/S1088424617500596Cited by:5 (Source: Crossref)

Abstract

Novel octa-phenotiazine, octa-benzoazepine and octa-carbazole substituted magnesium(II) (MgPz-I-III) and zinc(II) (ZnPz-I-III) porphyrazines were synthesized from 2,3-bis[6-(4a,10a-dihydro-phenothiazin-10-yl)-hexylsulfanyl]-but-2-enedinitrile (5), 2,3-bis [6-(4a,11a-dihydro-dibenzo[b,f]azepin-5-yl)-hexysulfan-yl]-but-2-enedinitrile (8) and 2,3-bis(6-carbazol-9-yl-hexylsulfanyl)-but-2-enedinitrile (10), respectively. These dinitrile derivatives 5, 8 and 10 were also prepared by the reaction of 1,2-dicyano-1,2-ethylenedithiolate di-sodium salt (4) with 10-(6-bromohexyl)-10H-phenothiazine (3), 5-(6-bromohexyl)-5H-diben-zo[b,f]azepine (7) and 9-(6-bromo-hexyl)-9H-carbazole (9), respectively. Porphyrazino-zinc(II) complexes were synthesized by one-step reaction using Zn(BuO) $_{2}$ as a template agent. All the novel compounds were characterized by elemental analysis and different spectroscopic methods such as $^{1}$ H NMR, $^{13}$ C NMR, FT-IR, UV-Vis and mass. The photochemical properties including photodegradation and singlet oxygen generation for magnesium(II) and zinc (II) porphyrazine complexes were studied in dimethylsulfoxide solutions for determination of their photosensitizer behaviors.

Keywords:

Most comprehensive & up-to-date research on PORPHYRINS
Handbook of Porphyrin Science now available in 46 volumes

References

1. (a) Mlynarczyk DT, Lijewski S, Falkowski M, Piskorz J, Szczolko W, Sobotta L, Stolarska M, Popenda L, Jurga S, Konopka K, Düzgüneş N, Mielcarek J and Goslinski T. ChemPlusChem. 2016; 81: 460–470; (b) Keskin B, Denktas C, Altınel A, Avcıata U and Gül A. Polyhedron 2012; 38: 121–125. (c) Schramn CJ and Hoffman BM. Inorg. Chem. 1980; 19: 383–385. (d) Andersen K, Anderson OP, Miller T, Mani NS, Baumann TF, Anderson M, Broderick WE, Eichhorn DM, Goldberg D, Jarrell W, Lange SJ, Lee S, Nie H, Sabat M, Sibert JW, Stern C, Hoffman BM, Baum S, Beall LS, Cook AS, Mccubbin QJ, Montalban AG, Rodriguez-Morgade MS, White AJP, Williams DBG, Williams DJ, Barrett AGM, Hope H and Olmstead MM. J. Heterocycl. Chem. 1998; 35: 1013–1042. (e) Lee S, White AJP, Williams DJ, Barrett AGM and Hoffman BM. J. Org. Chem. 2001; 66: 461–465. (f) Kayal H, Ahmida MM, Dufour S, Taing H and Eichhorn SH. J. Mater. Chem. 2013; 1: 7064–7072. (g) Song Y, Zong H, Trivedi ER, Vesper BJ, Waters EA Barrett AGM, Radosevich JA, Hoffman BM and Meade TJ. Bioconjugate Chem. 2010; 21: 2267–2275. Google Scholar
2. Hou R, Jin L and Yin B. Inorg. Chem. Commun. 2009; 12: 739–743. Crossref, Web of Science, Google Scholar
3. van Nostrum CF, Benneker FB, Brussaard H, Kooijman H, Veldman N, Spek AL, Schoonman J, Feiters MC and Nolte RJ. Inorg. Chem. 1996; 35: 959–969. Crossref, Web of Science, Google Scholar
4. (a) Michel SLJ, Barrett AGM and Hoffman BM. Inorg. Chem. 2003; 42: 814–820. (b) Veliizquez CS, Fox GA, Broderick WE, Andemen KA, Anderson OP, Barrett AGM and Hoffman BM. J. Am. Chem. Soc. 1992; 114: 7416–7424. Google Scholar
5. (a) Fuchter MJ, Zhang C, Zong H, Hoffman BM and Barrett AGM. Aust. J. Chem. 2008; 61: 235–255; (b) Bradley D, Williams G and Mbatha B. Dyes Pigments. 2011; 88: 65–74; (c) Sakellariou EG, Montalban AG, Beall LS, Henderson D $^{}$ Meunier HG, Phillips D, Suhling K, Barrett AGM and Hoffman BM. Tetrahedron 2003; 59: 9083–9090; (d) Montalban AG Jarrell W Riguet E McCubbin QJ Anderson ME White AJP Williams DJ Barrett AGM and Hoffman BM. J. Org. Chem. 2000; 65: 2472–2478; (e) Donzello MP, Ercolani C and Stuzhin PA. Coord. Chem. Rev. 2006; 250: 1530–1561; (f) Astruc D, (ed.) Electron transfer and radical processes in transition metal chemistry. New York: VCH; 1995; (g) Bonnet R. Chem. Soc. Rev. 1995; 24: 19–33; (h) Hanack M and Lang M. Advan. Mater. 1994; 6: 819–833; (i) Collins GE, Armstrong NR, Pankow JW, Oden C, Arbour C and Dodelet JP. J. Vac. Sci. Technol. A 1993; 11: 1383–1392; (j) Feucht C, Linssen T and Hanack M. Chem. Ber. 1994; 127: 113–117; (k) Falkowski M, Rebis T, Piskorz J, Popenda L, Jurga S, Mielcarek J, Milczarek G and Goslinski T. Dyes Pigments 2016; 134: 569–579; (l) Falkowski M, Rebis T, Piskorz J, Popenda L, Jurga S, Mielcarek J, Milczarek G and Goslinski T. J. Photochem. Photobiol. A 2015; 307–308: 54–67. Google Scholar
6. (a) Gratzel M. Inorg. Chem. 2005; 44: 6841–6851; (b) Koumura N, Wang ZS, Mori S, Miyashita M, Suzuki E and Hara K. J. Am. Chem. Soc. 2006; 128: 14256–14257; (c) Wang H, Zhang X, Gong F, Zhou G and Wang ZS. Adv. Mater. 2012; 24: 121–124; (d) Kimura M, Nomoto H, Masaki N and Mori S. Angew. Chem. Int. Ed. 2012; 51: 4371–4374. Google Scholar
7. (a) Srinivas K, Kumar CR, Reddy MA, Bhanuprakash K, Rao VJ and Giribabu L. Synth. Met. 2011; 161: 96–105; (b) Wang ZS, Koumura N, Cui Y, Takahashi M, Sekiguchi H, Mori A, Kubo T, Furube A and Hara K.Chem. Mater. 2008; 20: 3993–4003; (c) Hagfeldt A, Boschloo G, Sun L, Kloo L and Petterson H. Chem. Rev. 2010; 110: 6595–6663; (d) Bugatti V, Concilio S, Iannelli P, Piotto SP, Bellone S, Ferrara M, Neitzert HC, Rubino A, Sala DD and Vacca P. Synth. Met. 2006; 159: 13–20; (e) O’Regan B and Gratzel M. Nature 1991; 353: 737–740; (f) Hagfeldt A and Gratzel M. Chem. Rev. 1995; 95: 49–68. Google Scholar
8. (a) Chi Z, Zhang X, Xu B, Zhou X, Ma C, Zhang Y, Liu S and Xua J. Chem. Soc. Rev. 2012; 41: 3878–3896; (b) Barbarella G, Meluci M and Sotgiu G. Adv. Mater. 2005; 17: 1581–1593; (c) Ooyama Y, Inoue S, Nagano T, Kushimoto K, Ohshita J, Imae I, Komaguchi K and Harima Y. Angew. Chem. Int. Ed. 2011; 50: 7429–7433. Google Scholar
9. (a) Kim MS, Cho MJ, Choi YC Ahn KS, Choi DH, Kim K and Kim JH. Dyes Pigments 2013; 99: 986–994; (b) Silberg I, Cormos G and Onicui DC. Adv. Heterocycl. Chem. 2006; 90: 205–237; (c) Hua Y, Chang S, He J, Zhang C, Zhao J, Chen T, Wong WY, Wong WK, and Zhu X. Chem. Eur. J. 2014; 20: 6300–6308; (d) Sailer M, Nonnenmacher M, Oeser T and Müller TJJ. Eur. J. Org. Chem. 2006: 423–435. Google Scholar
10. (a) Goto T and Fujihara H. J. Mater. Sci. 2004; 39: 2171–2173; (b) Miles DT and Murray RW. Anal. Chem. 2001; 73: 921–929. Google Scholar
11. (a) Felmeister A and Discher CA. J. Pharm. Sci. 1964; 53: 756–762; (b) Wagner C. and Wagenknecht HA. Org. Biomol. Chem. 2008; 6: 48–50; (c) Valzelli L and Garattini S. in Principles of Psychopharmacology, (W.G. Clark, ed), Academic Press, New York, 1970; 255. Google Scholar
12. (a) Nagumo S, Mizukami M, Wada K, Miura T, Bando H, Kawahara N, Hashimoto Y, Miyashita M and Akita H. Tetrahedron Lett. 2007; 48: 8558–8561; (b) Mizukami M, Wada K, Sato G, Ishii Y and Kawahara N. Tetrahedron 2013; 69: 4120–4138; (c) Chen CT, Lin JS, Murthy VRKM, Lin YW, Yi W, Tao YT and Chien CH. Chem. Commun. 2005: 3980–3982. Google Scholar
13. (a) Wang CY, Li J, Cai SY, Ning Z, Zhao D, Zhang Q and Su JH, Dyes Pigments. 2012; 94: 40–48; (b) Zang XF, Xu YF, Iqbal Z, Huang ZS, Kuang DB, Wang L, Meier H, Li Y and Cao D. Dyes Pigments. 2013; 99: 1072–1081. Google Scholar
14. Perrin DD and Armarego WLF. Purification of Laboratory Chemicals, 2nd ed., Pergamon, Oxford, 1980. Google Scholar
15. (a) Davison A and Holm RH. Inorg. Synth. 1967; 6: 8–26; (b) Bahr G and Schleiter G. Chem. Ber. 1957; 90: 438–443. Google Scholar
16. (a) Lui J and Pei Q. Macromol. 2010; 43: 9608–9612; (b) Po SH Jen TH Chen YC, Hsiao AE, Yin SH, Chen HY and Chen SA. J. Am. Chem. Soc. 2008; 130: 4699–4707. Google Scholar
17. (a) Turdean R, Bogdan E, Terec A, Petran A, Vlase L, Turcu I and Grosu I. Central Eur. J. Chem. 2009; 7: 111–117; (b) Cho MJ, Lee SK, Jin JI, Choi DH and Dalton LR. Thin Solid Films 2006; 515: 2303–2309; (c) Susan MAH, Ishibashi A, Takeoka Y and Watanabe M. Coll. Surf. B: Biointerfaces 2004; 38: 167–173. Google Scholar
18. Seotsanyana-Mokhosi I, Kuznetsova N and Nyokong T. J. Photochem. Photobiol. A 2001; 140: 215–222. Crossref, Web of Science, Google Scholar
19. Kuznetsova NA, Gretsova NS, Kalmykova EA, Makarova EA, Dashkevich SN, Negrimovskii VM, Kaliya OL and Luk’yanets EA, Rus. J. Gen. Chem. 2000; 70: 133–140. Web of Science, Google Scholar
20. Spiller W, Kliesch H, Wöhrle D, Hackbarth S, Röder B and Schnurpfeil G. J. Porphyrins Phthalocyanines 1998; 2: 145–158. Link, Web of Science, Google Scholar
21. Marotta G, Reddy MA, Singh SP, Islam A, Han L, De Angelis F, Pastore M and Chandrasekharam M. Appl. Mater. Interfaces. 2013; 5: 9635–9647. Crossref, Web of Science, Google Scholar
22. (a) Chen Y and Wu TY. Polymer 2001; 42: 9895–9901; (b) Pouchert CJ, Behnke J. The Aldrich Library of $^{13}$ C and ¹H FT NMR Spectra, Vols. 3, Aldrich Chem. Co. Milwauke, 1993; 164A. Google Scholar
23. Linstead RP and Whalley M. J. Chem. Soc. 1952: 4839–4846. Crossref, Web of Science, Google Scholar
24. (a) Yıldırım Ö, Sevim AM and Gül A. Color. Tech. 2012; 128: 236–243; (b) Belviso S, Ricciardi G and Leji F. J. Mater. Chem. 2000; 10: 297–304; (c) Bilgin A, Ertem B and Gök Y. Dyes Pigments. 2009; 80: 187–193. Google Scholar
25. Kabay N, Karadeniz H, Demirayak N and Gök Y. Inorg. Chem. Commun. 2011; 14: 641–644. Crossref, Web of Science, Google Scholar
26. Rodriguez-Morgade MS and Stuzhin PA. J. Porphyrins Phthalocyanines 2004; 8: 1129–1165. Link, Web of Science, Google Scholar
27. Baygu Y, Yıldız B, Kabay N and Gök Y. Inorg. Chem. Commun. 2016; 71: 35–40. Crossref, Web of Science, Google Scholar
28. (a) Kabay N, Baygu Y, Alpoguz HK, Kaya A and Gök Y. Dyes Pigments. 2013; 96: 372–376; (b) Yıldız B, Baygu Y, Kara I, Dal H and Gök Y. Tetrahedron. 2016; 72: 6972–6981. Google Scholar
29. Karadeniz H and Gök Y. Dyes Pigments. 2008; 77: 351–356. Crossref, Web of Science, Google Scholar
30. Hans E and Roeland JMN. J. Porphyrins Phthalocyanines 2000; 4: 454-459. Link, Web of Science, Google Scholar
31. Dominquez DD, Snow AW, Shirk JS and Pong RGS. J. Porphyrins Phthalocyanines. 2001; 5: 582–592. Link, Web of Science, Google Scholar
32. Wieczorek E, Piskorz J, Popenda L, Jurga S, Mielcarek J and Goslinski T. Tetrahedron Lett. 2017; 58: 758–761. Crossref, Web of Science, Google Scholar
33. Piskorz J, Konopka K, Düzgüneş N, Gdaniec Z, Mielcarek J and Goslinski T. ChemMedChem. 2014; 9: 1775–1782. Crossref, Web of Science, Google Scholar
34. Piskorz J, Lijewski S, Gierszewski M, Gorniak K, Sobotta L, Wicher B, Tykarska E, Düzgüneş N, Konopka K, Sikorski M, Gdaniec M, Mielcarek J and Goslinski T. Dyes Pigments 2017; 136: 898–908. Crossref, Web of Science, Google Scholar
35. Kryjewski M, Tykarska E, Rebis T, Dlugaszewska J, Ratajczak M, Teubert A, Gapiński J, Patkowski A, Piskorz J, Milczarek G, Gdaniec M, Goslinski T and Mielcarek J. Polyhedron 2015; 98: 217–223. Crossref, Web of Science, Google Scholar
36. Sobotta L, Fita P, Szczolko W, Wrotynski M, Wierzchowski M, Goslinski T and Mielcareket J. J. Photochem. Photobiol. A 2013; 269: 9–16. Crossref, Web of Science, Google Scholar
37. Piskorz J, Skupin P, Lijewski S, Korpusinski M, Sciepura M, Konopka K, Sobiak S, Goslinski T and Mielcarek J. J. Fluorine Chem. 2012; 135: 265-271. Crossref, Web of Science, Google Scholar
38. Goslinski T, Osmalek T and Mielcarek J. Polyhedron 2009; 28: 3839-3843. Crossref, Web of Science, Google Scholar
39. Durmuş M, Photochemical and Photophysical Characterization, in Nyokong T, Ahsen V. (Eds.) Photosensitizers in Medicine, Environment, and Security, ISBN: 978-90-481-3872-2, Springer Dordrecht Heidelberg: London, New York, 2012. Google Scholar