SYNTHESIS, CHARACTERIZATION AND PHOTOPHYSICAL PROPERTIES OF EUROPIUM(III) PHTHALOCYANINES BEARING [4-(thiophen-3yl)-phenoxy]

Fatma Aytan Kılıçarslan; İbrahim Erden

SYNTHESIS, CHARACTERIZATION AND PHOTOPHYSICAL PROPERTIES OF EUROPIUM(III) PHTHALOCYANINES BEARING [4-(thiophen-3yl)-phenoxy]

Abstract

In this study, two novel phthalonitriles (1,4) and their corresponding metal-free (2,5) and Eu(III) phthalocyanine derivatives (3,6) bearing 4-(thiophen-3yl)-phenoxy groups were synthesized. These novel compounds were characterized by elemental analysis, FTIR, H NMR, UV-Vis, fluorescence, and mass spectroscopy. The aggregation behavior of these compounds was investigated in different solvents and concentrations. The effects of the substituent and the nature of the europium on the photophysical parameters are also reported.

Keywords

References

[1] Andre J, Holczer K, Petit P, Riou M J, Clarisse C, Even R, Fourmigue M, and Simon J, “Electrical and magnetic properties of thin films and single crystals of bis(phthalocyaninato)lutetium” Chem. Phys. Lett. 115, 463-466, 1985.
[2] De Cian A, Moussaui M, Fischer J, Weiss R, Inorganic Chem. “Synthesis, structure, and spectroscopic and magnetic properties of lutetium(III) phthalocyanine derivatives: LuPc2.CH2Cl2 and [LuPc(OAc)(H2O)2].H2O.2CH3OH”,24, 3162-3167,1985.
[3] Pandoven A, Cozien Y, L’Her M, New J. Chem. 16, 711-718,1992.
[4] Jiang J, Liu W, Poon K, Du D, Arnold D, Dennis KP, J. Inorg. Chem. “Synthesis, Spectroscopic, and Electrochemical Properties of Rare Earth Double Deckers with Tetra-(tertbutyl)-2,3-naphthalocyaninato Ligands”, 205-209, 2000.
[5] Kobayashi N, Coord. Chem. Rev. “Optically active phthalocyanines”, 219, 99-123, 2001.
[6] Toupance T, Bassoul P, Mineau L, Simon J, J. Phys. Chem. 100,1704-1713,1996.
[7] Kobayashi N, Current Opinion in Solid State and Materials Science, “phthalocyanines”, 4, 345-353, 1999.
[8] Ford WE, Rogers J, Schechtman L, Sounik JR, Inorganic Chem. Comm. 31, 3371-3376, 1992.

[9] Ceyhan T, Altındal A, Özkaya A, Erbil MK, Bekaroğlu Ö, “Synthesis, characterization, and electrochemical, electrical and gas sensing
properties of a novel tert-butylcalix[4]arene bridged bis double-decker lutetium(III) phthalocyanine” Polyhedron 26, 73-84, 2007.
[10] Şen P, Dumludağ F, Salih B, Özkaya A, Bekaroğlu Ö, “Synthesis and electrochemical, electrochromic and electrical properties of novel s-triazine bridged trinuclear Zn(II), Cu(II) and Lu(III) and a tris double-decker Lu(III) phthalocyanines”, Synthetic Metals 161, 1245- 1254, 2011.
[11] Bao G, Wang W, Mao Y, Lu F, “Raman spectroscopic characteristics of phthalocyanine in mixed [5-(4-hydroxyphenyl)-10,15,20- tris(4-octyloxyphenyl)porphyrinato]-(phthalocyaninato) rare earth triple-deckers”, Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 102, 275-280, 2013.
[12] Arıcı M, Bozoğlu C, Erdoğmuş A, Uğur AL, Koca A, “Electrochemical and spectroelectrochemical properties of novel lutetium(III) mono- and bis-phthalocyanines”, Elecrochimica Acta, 113, 668-678, 2013.
[13] Iwatsu F, Kobayashi T, Uyeda N, “Solvent effects on crystal-growth and transformation of zinc phthalocyanine” J. Phys. Chem. 84, 3223-3230, 1980.
[14] Erdogmus A, Koca A, Lütfi Ugur A, Erden I, “Synthesis, Electrochemical and Spectroelectrochemical Properties of Highly Soluble Tetra Substituted Phthalocyanines with [4-(Thiophen-3yl)-phenoxy]”, Synthetic Metals, 161, 1319-1329, 2011.
[15] Perrin DD, Armarego WL, Pegamon Press, Oxford, 1989.
[16] Erdogmus A, Nyokong T, “Synthesis, photophysical and photochemical properties of novel soluble tetra-4-(thiophen-3yl)-phenoxy-phthalocyaninato zinc(II) and Ti(IV)O complexes” Inorganica Chimica Acta, 362, 4875-4883, 2009.
[17] Özdemir M, Aytan Kılıçarslan F, Erdoğmuş A, Erden I, “Tetra- and octa-[4-(thiophen-3-yl)phenoxy]-bearing metal-free and Lu(III) phthalocyanines: synthesis, characterisation and investigation of photophysical properties” Journal of Chemical Research, 40, 250-254, 2016.
[18] Öztürk C, Erdoğmuş A, Durmuş M, Uğur A.L, Kılıçarslan F.A, Erden I, “Highly Soluble 3,4-(dimetoxyphenylthio) Substituted Phthalocyanines: Synthesis, Photophysical and Photochemical Studies” Spectrochimica Acta Part A 86, 423-.431, 2012.
[19] Yaşa G, Erdoğmuş A, Uğur A.L, Şener M.K, Avcıata U, Nyokong T, “Photophysical and photochemical properties of novel phthalocyanines bearing non-peripherally mercaptoquinoline moiety” J. Porphyrins Phthalocyanines 16, 845-854,2012.
[20] Erdoğmuş A , Ogunsipe A, Nyokong T, “Synthesis, photophysics and photochemistry of novel tetra(quinoxalinyl)phthalocyaninato
zinc(II) complexes” J. Photochem. Photobiol. 205, 12-18, 2009.
[21] Durmuş M, Yeşilot S, Çoşut B, Gül Gürek AG, Kılıç A, Ahsen V, “Comparison of photophysicochemical properties of hexaphenoxycyclotriphosphazenyl-substituted metal-free, mono and bis-lutetium phthalocyanines”, Synthetic Metals 160, 436-441, 2010.
[22] Senge MO, Renner MW, Kalisch WW, Fajer J, “Molecular structure of (5,10,15,20-tetrabutyl-2,3,7,8,12,13,17,18-octaethylporphyrinato) nickel(II)-correlation of nonplanarity with frontier orbital shifts” J. Chem. Soc., Dalton Trans. 381, 2000.
[23] Idowu M, Nyokong T, “Synthesis, photophysics and photochemistry of tin(IV) phthalocyanine derivatives” J. Photoch. Photobio. A: Chemistry 199, 282-290, 2008.
[24] Chauke V, Durmus M, Nyokong T, “Photochemistry, photophysics and nonlinear optical parameters of phenoxy and tert-butyl phenoxy substituted indium(III) phthalocyanines”, Journal of Photochemistry and Photobiology A: Chemistry 192, 179-187, 2007.

Details

Primary Language

English

Subjects

-

Journal Section

Research Article

Authors

Fatma Aytan Kılıçarslan This is me
Türkiye

İbrahim Erden This is me
Türkiye

Publication Date

March 1, 2017

Submission Date

August 11, 2016

Acceptance Date

December 13, 2016

Published in Issue

Year 2017 Volume: 35 Number: 1

IZ

https://izlik.org/JA67RL72RJ

Cite

RIS / Bibtex

APA

Aytan Kılıçarslan, F., & Erden, İ. (2017). SYNTHESIS, CHARACTERIZATION AND PHOTOPHYSICAL PROPERTIES OF EUROPIUM(III) PHTHALOCYANINES BEARING [4-(thiophen-3yl)-phenoxy]. Sigma Journal of Engineering and Natural Sciences, 35(1), 23-34. https://izlik.org/JA67RL72RJ

AMA

1.Aytan Kılıçarslan F, Erden İ. SYNTHESIS, CHARACTERIZATION AND PHOTOPHYSICAL PROPERTIES OF EUROPIUM(III) PHTHALOCYANINES BEARING [4-(thiophen-3yl)-phenoxy]. SIGMA. 2017;35(1):23-34. https://izlik.org/JA67RL72RJ

Chicago

Aytan Kılıçarslan, Fatma, and İbrahim Erden. 2017. “SYNTHESIS, CHARACTERIZATION AND PHOTOPHYSICAL PROPERTIES OF EUROPIUM(III) PHTHALOCYANINES BEARING [4-(thiophen-3yl)-Phenoxy]”. Sigma Journal of Engineering and Natural Sciences 35 (1): 23-34. https://izlik.org/JA67RL72RJ.

EndNote

Aytan Kılıçarslan F, Erden İ (March 1, 2017) SYNTHESIS, CHARACTERIZATION AND PHOTOPHYSICAL PROPERTIES OF EUROPIUM(III) PHTHALOCYANINES BEARING [4-(thiophen-3yl)-phenoxy]. Sigma Journal of Engineering and Natural Sciences 35 1 23–34.

IEEE

[1]F. Aytan Kılıçarslan and İ. Erden, “SYNTHESIS, CHARACTERIZATION AND PHOTOPHYSICAL PROPERTIES OF EUROPIUM(III) PHTHALOCYANINES BEARING [4-(thiophen-3yl)-phenoxy]”, SIGMA, vol. 35, no. 1, pp. 23–34, Mar. 2017, [Online]. Available: https://izlik.org/JA67RL72RJ

ISNAD

Aytan Kılıçarslan, Fatma - Erden, İbrahim. “SYNTHESIS, CHARACTERIZATION AND PHOTOPHYSICAL PROPERTIES OF EUROPIUM(III) PHTHALOCYANINES BEARING [4-(thiophen-3yl)-Phenoxy]”. Sigma Journal of Engineering and Natural Sciences 35/1 (March 1, 2017): 23-34. https://izlik.org/JA67RL72RJ.

JAMA

1.Aytan Kılıçarslan F, Erden İ. SYNTHESIS, CHARACTERIZATION AND PHOTOPHYSICAL PROPERTIES OF EUROPIUM(III) PHTHALOCYANINES BEARING [4-(thiophen-3yl)-phenoxy]. SIGMA. 2017;35:23–34.

MLA

Aytan Kılıçarslan, Fatma, and İbrahim Erden. “SYNTHESIS, CHARACTERIZATION AND PHOTOPHYSICAL PROPERTIES OF EUROPIUM(III) PHTHALOCYANINES BEARING [4-(thiophen-3yl)-Phenoxy]”. Sigma Journal of Engineering and Natural Sciences, vol. 35, no. 1, Mar. 2017, pp. 23-34, https://izlik.org/JA67RL72RJ.

Vancouver

1.Fatma Aytan Kılıçarslan, İbrahim Erden. SYNTHESIS, CHARACTERIZATION AND PHOTOPHYSICAL PROPERTIES OF EUROPIUM(III) PHTHALOCYANINES BEARING [4-(thiophen-3yl)-phenoxy]. SIGMA [Internet]. 2017 Mar. 1;35(1):23-34. Available from: https://izlik.org/JA67RL72RJ