SYNTHESIS, CHARACTERIZATION, SPECTRAL, AGGREGATION AND FLUORESCENCE AND IMPROVED PHOTOPHYSICAL PROPERTIES OF (ethylsulfanyl) PORPHYRAZINES CONTAINING β-THIOETHER APPENDED [(bpy)2RuCl2]

Fatma Aytan Kılıçarslan; Ali Erdoğmuş; Sabiha Manav Yalçın; Ahmet Gül

SYNTHESIS, CHARACTERIZATION, SPECTRAL, AGGREGATION AND FLUORESCENCE AND IMPROVED PHOTOPHYSICAL PROPERTIES OF (ethylsulfanyl) PORPHYRAZINES CONTAINING β-THIOETHER APPENDED [(bpy)2RuCl2]

Abstract

In this study, (ethylsulfanyl) porphyrazines have been modified with one peripheral ruthenium bipyridine groups. These compounds possess (bpy)2RuII moieties directly attached to the β position in the (ethylsulfanyl) porphyrazines through thioether chelation. The new compounds have been characterized by elemental analysis, FT-IR, 1H-NMR spectroscopy and mass spectra. The spectral properties such as electronic spectra, aggregation and fluorescence of compounds have been studied in THF. Insertion of (bpy)2RuII moiety on the porphyrazines structure have been investigated photophysical properties of the complexes.

Keywords

References

[1] Forsyth TP, Williams DBG, Montalban AG, Stern CL, Barret AGM, Hoffman BM, “A Facile and Regioselective Synthesis of Trans-Heterofunctionalized Porphyrazine Derivatives” J. Org. Chem., 63, 331, 1998.
[2] Cosimelli B, Roncucci G, Dei D, Fantetti L, Ferroni F, Ricci M, Spinelli D, “Synthesis and antimycotic activity of new unsymmetrical substituted zinc phthalocyanines” Tetrahedron, 59,10025-10030, 2003.
[3] Kubat P, Mosinger J. Photophysical properties of metal complexes of meso-tetrakis (4-sulphonatophenyl) porphyrin. J. Photochem. Photobiol. A: Chem. 96, 3-97,1996.
[4] Li G, Pandey SK, Graham A, Dobhal MP, Mehta R, Chem Y, Gryshuk A, Rittenhouse-Olson K, Oseroff A, Pandey RK, “Functionalization of OEP-based benzochlorins to develop carbohydrate-conjugated photosensitizers. Attempt to target beta-galactoside-recognized proteins” J. Org. Chem., 69,158-172, 2004.
[5] Montalban AG, Jarrell W, Riguet E, McCubbin QJ, Anderson ME, White AJP, Williams DJ, Barret AGM, Hoffman BM, “Bis(dimethylamino)porphyrazines: synthetic, structural, and spectroscopic investigations” J. Org. Chem., 65,2472, 2000 .
[6] Erdoğmuş A., Akınbulu IA., Nyokong T, “Synthesis and electrochemical properties of new cobalt and manganese phthalocyanine complexes tetra-substituted with 3,4-(methylendioxy)-phenoxy” Polyhedron, 29, 11, 2352-2363, 2010.
[7] Erdoğmuş A, Koca A, Avcıata U, Gül A, “Synthesis, Characterization and Electrochemistry of New Soluble Porphyrazine Complexes Bearing Octakis 3-Methylbutylthio Substituents” Z Anorg Chem., 634, 2649-2654, 2008.
[8] Kobayashi, N. In Phthalocyanines, Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH: New York, 1993; Vol.2, p 97.

[9] Van Nostrum CF, Nolte RJM, “Functional supramolecular materials: self-assembly of phthalocyanines and porphyrazines” Chem. Com., 2385-2392, 1996.
[10] Benniston AC, Grosshenny V, Harriman A, Ziessel R, “Photophysical properties of closely-coupled, binuclear ruthenium(II) bis(2,2′:6′,2″-terpyridine) complexes” Dalton Trans., 1227–1232, 2004.
[11] Tan LF, Chao H, Li H, Liu YJ, Sun B, Wei W, Ji LN, “Synthesis, characterization, DNA-binding and photocleavage studies of [Ru(bpy)2(PPIP)]2+ and [Ru(phen)2(PPIP)]2+” J. Inorg. Biochem., 99, 513–520, 2005.
[12] Smith JA, Collins JG, Patterson BT, Keene FR, “Total Enantioselectivity in the DNA Binding of the Dinuclear Ruthenium(II) Complex [{Ru(Me2bpy)2}2(μ-bpm)]4+ {bpm = 2,2'-bipyrimidine; Me2bpy = 4,4'-dimethyl-2,2'-bipyridine}” Dalton Trans., 1277–1283, 2004.
[13] Wu JZ, Yuan L, Yu Y, “Effect of copper ion on DNA intercalating behavior of a chelation unsaturated diruthenium polypyridyl complex” Inorg. Chim. Acta, 359, 718–720, 2006.
[14] Karidi K, Garoufis A, Hadjiliadis N, Reedijk J, “Solid-phase synthesis, characterization and DNA binding properties of the first chloro(polypyridyl)ruthenium conjugated peptide complex” Dalton Trans., 728–734, 2005.
[15] Karidi K, Reedijk J, Hadjiliadis N, Garoufis A. Synthesis, characterization and DNA binding properties of oligopyridine-ruthenium(II)-amino acid conjugates. J. Inorg. Biochem., 101, 2007.
[16] Vaidyanathan VG, Nair BU, “Synthesis, Characterization and DNA binding studies of a ruthenium (II) complex” J. Inorg. Biochem., 91,405–412, 2002.
[17] Oda M, Matsumura H. US Patent, US 6914276 B2, 2005.
[18] Hagemann O, Jorgensen M, Krebs FC, “Synthesis of an All-in-One Molecule (for Organic Solar Cells)” J. Org. Chem., 71, 5546, 2006.
[19] Juris A, Balzani V, Barigelletti F, Campagna S, Belser P, Von Zelewsky A, “Ru(II) polypyridine complexes - photophysics, photochemistry, electrochemistry, and chemiluminescence” Coord. Chem. Rev., 84, 85-277, 1988.
[20] Venturi M, Marchioni F, Balzani V, Opris DM, Henze O, Schluter AD, “A photophysical and electrochemical investigation on a phenylacetylene macrocycle containing two 2,2’-bipyridine units, its protonated forms, and Ru(II) and Os(II) complexes” Eur. J. Org. Chem., 21,4227- 4233, 2003.
[21] Prasad R, Kumar A, “Synthesis, spectroscopic and electrochemical investigations of supramolecular nickel(II)tetraazaporphyrin complexes” J. Porph. Phthal., 2005;9:509.
[22] Prasad R, Kumar A, “Spectroscopic and electrochemical investigation of coordination complexes of octakis(benzylthio)tetraazaporphyrincobalt(II)” Inorg. Chem. Acta, 358, 3201, 2005.
[23] Prasad R, Kumar A, Gupta VK, “Magnesium–tetrazaporphyrin incorporated PVC matrix as a new material for fabrication of Mg2+ selective potentiometric sensor” Talanta, 63,1027, 2004.
[24] Kumar R.; Kumar, A, “Stepwise synthesis of peripherally dimetallated metallo-tetraazaporphyrins with linear and bent motifs” Transit. Metal Chem, 32, 1091-1095, 2007.
[25] Morisaki Y, Kondo T, Mitsudo T, “Ruthenium-Catalyzed Allylic Substitution of Cyclic Allyl Carbonates with Nucleophiles. Stereoselectivity and Scope of the Reaction” Organometallics, 18, 4742, 1999.
[26] Plault L, Hauseler A, Nlate S, Astruc D, Ruiz J, Gatard S, Neumann R, “Synthesis of dendritic polyoxometalate complexes assembled by ionic bonding and their function as recoverable and reusable oxidation catalysts” Angew. Chem., Int. Ed., 43, 2924-2928, 2004.
[27] Öztürk R, Gül A, “Construction of nonanuclear supramolecular structures from simple modular units” Tetrahedron Lett, 45, 947-949, 2004.
[28] Bahr G, Schleitzer G, “Die Kondenzieren Spontanentschwefelung von Salzen und Estern der Cyandithioameisen-Soure. Freie Cyan Dithioameisensoure” Chem. Ber, 10, 8-26, 1967.
[29] Lelj F, Morelli G, Ricciardi G, Rovıello A, Sırıgu A, “Discotic mesomorphism of 2,3,7,8,12,13,17,18-octakis (alkyl-thio) 5,10,15,20 tetraaza porphyrin and its complexes with some divalent transition metal ions Synthesis and characterization” Liq. Cryst, 12, 941-960, 1992.
[30] Belviso S, Ricciardi G, Lelj F, “’Inter-ring İnteractions and Peripheral Tail Effects on the Discotic Mezomorphism of `free-base`and Co (II), Ni (II) and Cu (II) Alkenly Porphyrazine” J. Mater. Chem, 10, 297-304, 2000.
[31] Akkurt M, Coşkun NY, Kılıçarslan FA, Yalçın SM, Büyükgüngör O, Gül A. “[2,3,7,8,13,14,17,18-Octakis(ethyl-sulfanyl)-5,10,15,20-porphyrazinato]-zinc(II)” Acta Cryst. 2010, E66, M998-m999.
[32] Frey-Forgues S, Lavabre D, “Are fluorescence quantum yields so tricky to measure? A demonstration using familiar stationery products” J. Chem. Educ., 76, 1260-1264, 1999.
[33] Öztürk C, Erdoğmuş A, Durmuş M, Uğur AL, Kılıçarslan FA, Erden İ, “Highly soluble 3,4-(dimethoxyphenylthio) substituted phthalocyanines: Synthesis, photophysical and photochemical studies” Spectrochim Acta A, 86,423-431, 2012.
[34] Saka ET, Göl C, Durmuş M, Kantekin H, Bıyıklıoğlu Z, “Photophysical, photochemical and aggregation behavior of novel peripherally tetra-substituted phthalocyanine derivatives”. J. Photochem. Photobiol. A: Chem, 241, 67-78, 2012 .
[35] Gan, Q.; Xiong, F.; Li, S.; Wang, S, “Synthesis and Photophysical Properties of a Series of OctaphenylPorphyrazine–Magnesium” Inorg. Chem. Commun., 8,285-288, 2005.
[36] Kılıçarslan FA, Erdoğmuş A, Coşkun NY, Yalçın SM, Gül A, “Synthesis, spectral and photophysical investigation of porphyrazines with eight 3-quinolinecarboxy esters” J. Coord. Chem., 66, 24, 4316-4329, 2013.
[37] Erdoğmuş, A, Nyokong, T, “Novel, soluble, FluXoro functional substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties” Dyes Pigments, 86, 174-181, 2010.
[38] Erdoğmuş A, Moeno S, Litwinski C, Nyokong T, “Photophysical properties of newly synthesized fluorinated zinc phthalocyanines in the presence of CdTe quantum dots and the accompanying energy transfer processes” J. Photochem. and Photobiol. A: Chem., 210, 200-208, 2010.
[39] Atmaca G.Y, Dizman C, T, Erdoğmuş A,, Novel axially carborane-cage substituted silicon phthalocyanine photosensitizer; synthesis, characterization and photophysicochemical properties, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 137, 244-249, 2015.
[40] Nyokong T, Antunes E, in: K.M. Kadish, K.M. Smith, R. Guilard (Eds.), The Handbook of Porphyrin Science, vol. 7, Academic Press/World Scientific, New York/Singapore, 2010, 34, 247.
[41] Kırbaç E, Atmaca G.Y, Erdoğmuş A, “Novel highly soluble fluoro, chloro, bromo-phenoxy-phenoxy substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties” Journal of Organometallic Chemistry, 752, 115-122, 2014.
[42] Erdoğmuş A,, Ogunsıpe A., Nyokong T, “Synthesis, photophysics and photochemistry of novel tetra(quinoxalinyl)phthalocyaninato zinc(II) complexes” Journal of Photochemistry and Photobiology A: Chemistry, 205,1, 12-18, 2009.
[43] Sezer B, Şener MK, Koca A, Erdoğmuş A,, Avcıata U, “Synthesis, Electrochemistry, Spectroelectrochemistry and Electrocolorimetry of Phthalocyanine-Anthraquinone Dyads” Synthetic Metals, 160, 19, 2155-2166, 2010.

Details

Primary Language

English

Subjects

-

Journal Section

Research Article

Authors

Fatma Aytan Kılıçarslan This is me
0000-0002-4623-3067
Türkiye

Ali Erdoğmuş This is me
0000-0001-9282-7651
Türkiye

Sabiha Manav Yalçın This is me
Türkiye

Ahmet Gül This is me
Türkiye

Publication Date

June 1, 2018

Submission Date

November 14, 2017

Acceptance Date

February 16, 2018

Published in Issue

Year 2018 Volume: 36 Number: 2

IZ

https://izlik.org/JA64PW28EP

Cite

RIS / Bibtex

APA

Kılıçarslan, F. A., Erdoğmuş, A., Manav Yalçın, S., & Gül, A. (2018). SYNTHESIS, CHARACTERIZATION, SPECTRAL, AGGREGATION AND FLUORESCENCE AND IMPROVED PHOTOPHYSICAL PROPERTIES OF (ethylsulfanyl) PORPHYRAZINES CONTAINING β-THIOETHER APPENDED [(bpy)2RuCl2]. Sigma Journal of Engineering and Natural Sciences, 36(2), 487-499. https://izlik.org/JA64PW28EP

AMA

1.Kılıçarslan FA, Erdoğmuş A, Manav Yalçın S, Gül A. SYNTHESIS, CHARACTERIZATION, SPECTRAL, AGGREGATION AND FLUORESCENCE AND IMPROVED PHOTOPHYSICAL PROPERTIES OF (ethylsulfanyl) PORPHYRAZINES CONTAINING β-THIOETHER APPENDED [(bpy)2RuCl2]. SIGMA. 2018;36(2):487-499. https://izlik.org/JA64PW28EP

Chicago

Kılıçarslan, Fatma Aytan, Ali Erdoğmuş, Sabiha Manav Yalçın, and Ahmet Gül. 2018. “SYNTHESIS, CHARACTERIZATION, SPECTRAL, AGGREGATION AND FLUORESCENCE AND IMPROVED PHOTOPHYSICAL PROPERTIES OF (ethylsulfanyl) PORPHYRAZINES CONTAINING β-THIOETHER APPENDED [(bpy)2RuCl2]”. Sigma Journal of Engineering and Natural Sciences 36 (2): 487-99. https://izlik.org/JA64PW28EP.

EndNote

Kılıçarslan FA, Erdoğmuş A, Manav Yalçın S, Gül A (June 1, 2018) SYNTHESIS, CHARACTERIZATION, SPECTRAL, AGGREGATION AND FLUORESCENCE AND IMPROVED PHOTOPHYSICAL PROPERTIES OF (ethylsulfanyl) PORPHYRAZINES CONTAINING β-THIOETHER APPENDED [(bpy)2RuCl2]. Sigma Journal of Engineering and Natural Sciences 36 2 487–499.

IEEE

[1]F. A. Kılıçarslan, A. Erdoğmuş, S. Manav Yalçın, and A. Gül, “SYNTHESIS, CHARACTERIZATION, SPECTRAL, AGGREGATION AND FLUORESCENCE AND IMPROVED PHOTOPHYSICAL PROPERTIES OF (ethylsulfanyl) PORPHYRAZINES CONTAINING β-THIOETHER APPENDED [(bpy)2RuCl2]”, SIGMA, vol. 36, no. 2, pp. 487–499, June 2018, [Online]. Available: https://izlik.org/JA64PW28EP

ISNAD

Kılıçarslan, Fatma Aytan - Erdoğmuş, Ali - Manav Yalçın, Sabiha - Gül, Ahmet. “SYNTHESIS, CHARACTERIZATION, SPECTRAL, AGGREGATION AND FLUORESCENCE AND IMPROVED PHOTOPHYSICAL PROPERTIES OF (ethylsulfanyl) PORPHYRAZINES CONTAINING β-THIOETHER APPENDED [(bpy)2RuCl2]”. Sigma Journal of Engineering and Natural Sciences 36/2 (June 1, 2018): 487-499. https://izlik.org/JA64PW28EP.

JAMA

1.Kılıçarslan FA, Erdoğmuş A, Manav Yalçın S, Gül A. SYNTHESIS, CHARACTERIZATION, SPECTRAL, AGGREGATION AND FLUORESCENCE AND IMPROVED PHOTOPHYSICAL PROPERTIES OF (ethylsulfanyl) PORPHYRAZINES CONTAINING β-THIOETHER APPENDED [(bpy)2RuCl2]. SIGMA. 2018;36:487–499.

MLA

Kılıçarslan, Fatma Aytan, et al. “SYNTHESIS, CHARACTERIZATION, SPECTRAL, AGGREGATION AND FLUORESCENCE AND IMPROVED PHOTOPHYSICAL PROPERTIES OF (ethylsulfanyl) PORPHYRAZINES CONTAINING β-THIOETHER APPENDED [(bpy)2RuCl2]”. Sigma Journal of Engineering and Natural Sciences, vol. 36, no. 2, June 2018, pp. 487-99, https://izlik.org/JA64PW28EP.

Vancouver

1.Fatma Aytan Kılıçarslan, Ali Erdoğmuş, Sabiha Manav Yalçın, Ahmet Gül. SYNTHESIS, CHARACTERIZATION, SPECTRAL, AGGREGATION AND FLUORESCENCE AND IMPROVED PHOTOPHYSICAL PROPERTIES OF (ethylsulfanyl) PORPHYRAZINES CONTAINING β-THIOETHER APPENDED [(bpy)2RuCl2]. SIGMA [Internet]. 2018 Jun. 1;36(2):487-99. Available from: https://izlik.org/JA64PW28EP