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Aksiyel (oksietil)pirolidin İkameli Silisyum(IV) Ftalosiyaninin Sentezi, Yapısal Karakterizasyonu, Agregasyon ve Fotobozunma özelliklerinin incelenmesi

Year 2021, Volume: 11 Issue: 1, 345 - 352, 01.03.2021
https://doi.org/10.21597/jist.738714

Abstract

Bu çalışmada, (oksietil)pirolidin grupları ile eksenel olarak ikame edilmiş yeni bir silikon(IV)ftalosiyanin sentezlenmiş ve karakterize edilmiştir. Yeni saflaştırılmış bileşik, element analizi, FT-IR, UV-Vis, 1H-NMR ve MALDI-TOF kütle spektrometrisi gibi standart karakterizasyon teknikleri ile karakterize edildi. Elde edilen silikon(IV) ftalosiyanin, aseton, diklorometan, kloroform, piridin, DMF, DMSO ve etil asetat gibi organik çözücülerde mükemmel çözünürlük göstermiştir. Ayrıca, yeni silikon (IV) ftalosiyaninin agregasyon ve fotobozunma özellikleri incelenmiştir. Sentezlenen yeni ftalosiyanin bileşiği agregasyon göstermemiştir.

References

  • Balcı M, 2007. Nükleer Manyetik Rezonans Spektroskopisi. METU yayınları. ISBN: 9757064238
  • Braichotte DR, Savary JF, Monnier P, van den Bergh HE, 1996. Optimizing light dosimetry in photodynamic therapy of early stage carcinomas of the esophagus using fluorescence spectroscopy. Lasers Surgery and Medicine, 19: 340–346.
  • Cheng G, Peng X, Hao G, Kennedy VO, Ivanov IN, Knappenberger K, Hill TJ, Rodgers MAJ, Kenney ME, 2003.Synthesis, Photochemistry, and Electrochemistry of a Series of Phthalocyanines with Graded Steric Hindrance.J. Phys. Chem. A, 107: 3503–3514.
  • Dominguez DD, Snow AW, Shirk JS, Pong RG.S, 2001.Polyethyleneoxide-capped phthalocyanines:limiting phthalocyanine aggrega-tion to dimer formation.Journal Porphyrins Phthalocyanines, 5: 582–592.
  • DumoulinF. Design and Conception of Photosensitisers. Bölüm 1, sayfa1-46,2012. Photosensitizers in Medicine, Environment, and Security. Editör: Tebello Nyokong • Vefa Ahsen. Springer Dordrecht Heidelberg London New York. Doi:10.1007/978-90-481-3872-2. e-ISBN 978-90-481-3872-2.
  • Durmuş M. 2012. Photosensitizers in Medicine, Environment, and Security. Bölüm 4, sayfa 135-266. Editors: Tebello Nyokong, Vefa Ahsen. Springer Dordrecht Heidelberg London New York. 2012. e-ISBN 978-90-481-3872-2. DOI 10.1007/978-90-481-3872-2.
  • Ertem B, Yalazan H, Güngör Ö, Sarkı G, Durmuş M, Saka ET, Kantekin H, 2018. Synthesis, structural characterization, and investigation on photophysical and photochemical features of new metallophthalocyanines.Journal of Luminescence, 204: 467-471.
  • Gillenwater A, Jacob R, Kortum RR, 1998. Fluorescence spectroscopy: A technique with potential to improve the early detection of aerodigestive tract neoplasia. Head Neck, 20: 556–562.
  • Guillaud G, Simon J, Germain JP, 1998.Metallophthalocyanines: Gas sensors, resistors and field effect transistors. Coord. Chem. Rev., 178: 1433–1484.
  • Gürol I, Durmuş M, Ahsen V, Nyokong T, 2007. Synthesis, photophysical and photochemical properties of substituted zinc phthalocyanines. Dalton Trans., 34: 3782-3791.
  • Gürol İ, Gümüş G, Tarakci DK, Güngör Ö, Durmuş M, Ahsen V, 2018. Photophysical and photochemical properties of fluoroether-substituted zinc (II) and titanium (IV) phthalocyanines. Journal of Porphyrins and Phthalocyanines. 22: 46–55.
  • Güngör Ö, Durmuş M, Ahsen V, 2016. Investigation of photochemical and photophysical properties of novel silicon(IV) phthalocyanines and their -oxo dimers. Turkish Journal of Chemistry, 41: 803-812.
  • Güngör Ö, Özpınar GA, DurmuşM, AhsenV, 2016.The effect of “on/off” molecular switching on the photophysical and photochemical properties of axially calixarene substituted activatable silicon(IV)phthalocyanine photosensitizers. Dalton Transactions, 45: 7634-7641.
  • Leznoff CC, Lever ABP, 1996. In Phthalocyanines: Properties and Applications; Rosenthal. I. Ed. VCH Publishers: New York, NY, USA, pp. 481-514.ISBN: 1-56081-544-2.
  • Loi MA, Neugebauer H, Denk P, Brabec CJ, Sariciftci NS, Gouloumis A, Vázquez P, Torres T, 2003 Long-lived photoinduced charge separation for solar cell applications in phthalocyanine–fulleropyrrolidine dyad thin films. J. Mater. Chem., 13: 700–704.
  • Lowery BMK, Starshak AJ, Esposito JN, Krueger PC, Kenney ME, 1964.Dichloro(phthalocyanino)silicon, Inorganic Chemistry, 4: 128.
  • Pan H, Chen C, Wang K, Li W, Jiang J, 2015.Unsymmetrical Pyrene‐Fused Phthalocyanine Derivatives: Synthesis, Structure, and Properties.Chem. Eur. J., 21: 3168–3173.
  • Schnurpfeil G, Sobbi AK, Spiller W, Kliesch H, Wöhrle D, 1997. Photo-oxidative stability and its correlation with semi-empirical MO calculations of various tetraazaporphyrin derivatives in solution. J Porphyrins Phthalocyanines, 1:159–167.
  • Ulmann S, 1992. Encyclopedia of Industrial Chemistry. Journal of Porfirin and Phthalocyanines, 5:213.
  • Wheeler BL, Nagasubramanian G, Bard AJ, Schectman LA, Dininny DR, Kenney ME, 1984. A silicon phthalocyanine and a silicon naphthalocyanine: synthesis, electrochemistry, and electrogenerated chemiluminescence. J. Am. Chem. Soc., 106: 7404-7410.
  • Yuksel F, Durmuş M, Ahsen V, 2011 Photophysical, photochemical and liquid-crystalline properties of novel gallium(III) phthalocyanines.Dyes and Pigments, 90: 191–200.
  • Zhang W, Ishimaru A, Onouchi H, Rai R, Saxena A, Ohira A, Ishikawa M, Naito M, Fujiki M, 2010. Ambidextrous optically active copper(ii) phthalocyanine supramolecules induced by peripheral group homochirality.New J. Chem., 34: 2310–2318.

Synthesis, Structural Characterization of Axial (oxyethyl)pyrrolidine Substituted Silicon(IV) Phthalocyanine and Investigation Aggregation and Photodegradation Properties

Year 2021, Volume: 11 Issue: 1, 345 - 352, 01.03.2021
https://doi.org/10.21597/jist.738714

Abstract

In this study, a novel silicon(IV) phthalocyanine axially substituted with (oxyethyl)pyrrolidine groups was synthesized and characterized. The novel purified compound was characterized by standard characterization techniques such as elemental analysis, FT-IR, UV-Vis, 1H-NMR and MALDI-TOF mass spectrometry. Obtained silicon(IV)phthalocyanine showed excellent solubility in organic solvents such as acetone, dichloromethane, chloroform, pyridine, DMF, DMSO and ethyl acetate. Also, aggregation and photodegregation features of novel silicon(IV)phthalocyanine were investigated. The synthesized new phthalocyanine compound did not show aggregation.

References

  • Balcı M, 2007. Nükleer Manyetik Rezonans Spektroskopisi. METU yayınları. ISBN: 9757064238
  • Braichotte DR, Savary JF, Monnier P, van den Bergh HE, 1996. Optimizing light dosimetry in photodynamic therapy of early stage carcinomas of the esophagus using fluorescence spectroscopy. Lasers Surgery and Medicine, 19: 340–346.
  • Cheng G, Peng X, Hao G, Kennedy VO, Ivanov IN, Knappenberger K, Hill TJ, Rodgers MAJ, Kenney ME, 2003.Synthesis, Photochemistry, and Electrochemistry of a Series of Phthalocyanines with Graded Steric Hindrance.J. Phys. Chem. A, 107: 3503–3514.
  • Dominguez DD, Snow AW, Shirk JS, Pong RG.S, 2001.Polyethyleneoxide-capped phthalocyanines:limiting phthalocyanine aggrega-tion to dimer formation.Journal Porphyrins Phthalocyanines, 5: 582–592.
  • DumoulinF. Design and Conception of Photosensitisers. Bölüm 1, sayfa1-46,2012. Photosensitizers in Medicine, Environment, and Security. Editör: Tebello Nyokong • Vefa Ahsen. Springer Dordrecht Heidelberg London New York. Doi:10.1007/978-90-481-3872-2. e-ISBN 978-90-481-3872-2.
  • Durmuş M. 2012. Photosensitizers in Medicine, Environment, and Security. Bölüm 4, sayfa 135-266. Editors: Tebello Nyokong, Vefa Ahsen. Springer Dordrecht Heidelberg London New York. 2012. e-ISBN 978-90-481-3872-2. DOI 10.1007/978-90-481-3872-2.
  • Ertem B, Yalazan H, Güngör Ö, Sarkı G, Durmuş M, Saka ET, Kantekin H, 2018. Synthesis, structural characterization, and investigation on photophysical and photochemical features of new metallophthalocyanines.Journal of Luminescence, 204: 467-471.
  • Gillenwater A, Jacob R, Kortum RR, 1998. Fluorescence spectroscopy: A technique with potential to improve the early detection of aerodigestive tract neoplasia. Head Neck, 20: 556–562.
  • Guillaud G, Simon J, Germain JP, 1998.Metallophthalocyanines: Gas sensors, resistors and field effect transistors. Coord. Chem. Rev., 178: 1433–1484.
  • Gürol I, Durmuş M, Ahsen V, Nyokong T, 2007. Synthesis, photophysical and photochemical properties of substituted zinc phthalocyanines. Dalton Trans., 34: 3782-3791.
  • Gürol İ, Gümüş G, Tarakci DK, Güngör Ö, Durmuş M, Ahsen V, 2018. Photophysical and photochemical properties of fluoroether-substituted zinc (II) and titanium (IV) phthalocyanines. Journal of Porphyrins and Phthalocyanines. 22: 46–55.
  • Güngör Ö, Durmuş M, Ahsen V, 2016. Investigation of photochemical and photophysical properties of novel silicon(IV) phthalocyanines and their -oxo dimers. Turkish Journal of Chemistry, 41: 803-812.
  • Güngör Ö, Özpınar GA, DurmuşM, AhsenV, 2016.The effect of “on/off” molecular switching on the photophysical and photochemical properties of axially calixarene substituted activatable silicon(IV)phthalocyanine photosensitizers. Dalton Transactions, 45: 7634-7641.
  • Leznoff CC, Lever ABP, 1996. In Phthalocyanines: Properties and Applications; Rosenthal. I. Ed. VCH Publishers: New York, NY, USA, pp. 481-514.ISBN: 1-56081-544-2.
  • Loi MA, Neugebauer H, Denk P, Brabec CJ, Sariciftci NS, Gouloumis A, Vázquez P, Torres T, 2003 Long-lived photoinduced charge separation for solar cell applications in phthalocyanine–fulleropyrrolidine dyad thin films. J. Mater. Chem., 13: 700–704.
  • Lowery BMK, Starshak AJ, Esposito JN, Krueger PC, Kenney ME, 1964.Dichloro(phthalocyanino)silicon, Inorganic Chemistry, 4: 128.
  • Pan H, Chen C, Wang K, Li W, Jiang J, 2015.Unsymmetrical Pyrene‐Fused Phthalocyanine Derivatives: Synthesis, Structure, and Properties.Chem. Eur. J., 21: 3168–3173.
  • Schnurpfeil G, Sobbi AK, Spiller W, Kliesch H, Wöhrle D, 1997. Photo-oxidative stability and its correlation with semi-empirical MO calculations of various tetraazaporphyrin derivatives in solution. J Porphyrins Phthalocyanines, 1:159–167.
  • Ulmann S, 1992. Encyclopedia of Industrial Chemistry. Journal of Porfirin and Phthalocyanines, 5:213.
  • Wheeler BL, Nagasubramanian G, Bard AJ, Schectman LA, Dininny DR, Kenney ME, 1984. A silicon phthalocyanine and a silicon naphthalocyanine: synthesis, electrochemistry, and electrogenerated chemiluminescence. J. Am. Chem. Soc., 106: 7404-7410.
  • Yuksel F, Durmuş M, Ahsen V, 2011 Photophysical, photochemical and liquid-crystalline properties of novel gallium(III) phthalocyanines.Dyes and Pigments, 90: 191–200.
  • Zhang W, Ishimaru A, Onouchi H, Rai R, Saxena A, Ohira A, Ishikawa M, Naito M, Fujiki M, 2010. Ambidextrous optically active copper(ii) phthalocyanine supramolecules induced by peripheral group homochirality.New J. Chem., 34: 2310–2318.
There are 22 citations in total.

Details

Primary Language Turkish
Subjects Chemical Engineering
Journal Section Kimya / Chemistry
Authors

Ömer Güngör 0000-0002-3835-2920

Publication Date March 1, 2021
Submission Date May 17, 2020
Acceptance Date September 3, 2020
Published in Issue Year 2021 Volume: 11 Issue: 1

Cite

APA Güngör, Ö. (2021). Aksiyel (oksietil)pirolidin İkameli Silisyum(IV) Ftalosiyaninin Sentezi, Yapısal Karakterizasyonu, Agregasyon ve Fotobozunma özelliklerinin incelenmesi. Journal of the Institute of Science and Technology, 11(1), 345-352. https://doi.org/10.21597/jist.738714
AMA Güngör Ö. Aksiyel (oksietil)pirolidin İkameli Silisyum(IV) Ftalosiyaninin Sentezi, Yapısal Karakterizasyonu, Agregasyon ve Fotobozunma özelliklerinin incelenmesi. J. Inst. Sci. and Tech. March 2021;11(1):345-352. doi:10.21597/jist.738714
Chicago Güngör, Ömer. “Aksiyel (oksietil)pirolidin İkameli Silisyum(IV) Ftalosiyaninin Sentezi, Yapısal Karakterizasyonu, Agregasyon Ve Fotobozunma özelliklerinin Incelenmesi”. Journal of the Institute of Science and Technology 11, no. 1 (March 2021): 345-52. https://doi.org/10.21597/jist.738714.
EndNote Güngör Ö (March 1, 2021) Aksiyel (oksietil)pirolidin İkameli Silisyum(IV) Ftalosiyaninin Sentezi, Yapısal Karakterizasyonu, Agregasyon ve Fotobozunma özelliklerinin incelenmesi. Journal of the Institute of Science and Technology 11 1 345–352.
IEEE Ö. Güngör, “Aksiyel (oksietil)pirolidin İkameli Silisyum(IV) Ftalosiyaninin Sentezi, Yapısal Karakterizasyonu, Agregasyon ve Fotobozunma özelliklerinin incelenmesi”, J. Inst. Sci. and Tech., vol. 11, no. 1, pp. 345–352, 2021, doi: 10.21597/jist.738714.
ISNAD Güngör, Ömer. “Aksiyel (oksietil)pirolidin İkameli Silisyum(IV) Ftalosiyaninin Sentezi, Yapısal Karakterizasyonu, Agregasyon Ve Fotobozunma özelliklerinin Incelenmesi”. Journal of the Institute of Science and Technology 11/1 (March 2021), 345-352. https://doi.org/10.21597/jist.738714.
JAMA Güngör Ö. Aksiyel (oksietil)pirolidin İkameli Silisyum(IV) Ftalosiyaninin Sentezi, Yapısal Karakterizasyonu, Agregasyon ve Fotobozunma özelliklerinin incelenmesi. J. Inst. Sci. and Tech. 2021;11:345–352.
MLA Güngör, Ömer. “Aksiyel (oksietil)pirolidin İkameli Silisyum(IV) Ftalosiyaninin Sentezi, Yapısal Karakterizasyonu, Agregasyon Ve Fotobozunma özelliklerinin Incelenmesi”. Journal of the Institute of Science and Technology, vol. 11, no. 1, 2021, pp. 345-52, doi:10.21597/jist.738714.
Vancouver Güngör Ö. Aksiyel (oksietil)pirolidin İkameli Silisyum(IV) Ftalosiyaninin Sentezi, Yapısal Karakterizasyonu, Agregasyon ve Fotobozunma özelliklerinin incelenmesi. J. Inst. Sci. and Tech. 2021;11(1):345-52.