ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

Tetrahydroquinoxaline based squaraines: Synthesis and photophysical properties

Chandrasekaran, Yogesh and Dutta, Gitish K and Kanth, Raja Bhaskar and Patil, Satish (2009) Tetrahydroquinoxaline based squaraines: Synthesis and photophysical properties. In: Dyes and Pigments, 83 (2). pp. 162-167.

[img] PDF
http___www.sciencedirect.com_science__ob=MImg&_imagekey=B6TFY-4W3HX7M-2-R&_cdi=5239&_user=512776&_orig=search&_coverDate=11%2F30%2F2009&_sk=999169997&view=c&wchp=dGLbVlW-zSkzS&md5=990c0f1c00498a6bcle.pdf - Published Version
Restricted to Registered users only

Download (413Kb) | Request a copy
Official URL: http://www.sciencedirect.com/science?_ob=ArticleUR...


Tetrahydroquinoxaline based squaraine dyes synthesized by the condensation reaction between squaric acid and different tetrahydroquinoxaline derivatives are described. The squaraines gave a strong intense peak at 700 nm and were found to exhibit good molar extinction coefficient (>105 M−1 cm−1). Metal binding studies were carried out with different metal ions and it was found that it was selective in the case of copper metal. Using Job's plot it was ascertained that the squaraines bind to the copper metal in the ratio of 2:1.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier Science.
Keywords: NIR dyes; Squaraines; Tetrahydroquinoxaline; Donor-acceptor-donor; Bathochromic shift; Job's plot [4] Beverina L, Abbotto A, Landenna M, Cerminara M, Tubino R, Meinardi F, et al. New p-extended water-soluble squaraines as singlet oxygen generators. Org Lett 2005;7:4257. [5] Jyothish K, Rekha R, Avirah R, Ramaiah D. Development of squaraine dyes for photodynamic therapeutical applications: synthesis and study of electronic factors in the dye formation reaction. Arkivoc 2007;8:296. [6] Ramaiah D, Joy A, Chandrasekhar N, Eldho NV, Das S, George MV. Halogenated squaraine dyes as potential photochemotherapeutic agents. Synthesis and study of photophysical properties and quantum efficiencies of singlet oxygen generation. Photochem Photobiol 1997;65:783. [7] Ramaiah D, Eckert I, Arun KT, Weidenfeller L, Epe B. Squaraine dyes for photodynamic therapy: study of their cytotoxicity and genotoxicity in bacteria and mammalian cells. Photochem Photobiol 2002;76:672. [8] Ramaiah D, Eckert I, Arun KT, Weidenfeller L, Epe B. Squaraine dyes for photodynamic therapy: mechanism of cytotoxicity and DNA damage induced by halogenated squaraine dyes plus light (>600 nm). PhotochemPhotobiol 2004;79:99. [9] Suzuki Y, Yokoyama K. A protein-responsive chromophore based on squaraine and its application to visual protein detection on a gel for SDS-PAGE. Angew Chem Int Ed 2007;46:4097. [10] Jisha VS, Arun TK, Hariharan M, Ramaiah D. Site-selective binding and dual mode recognition of serum albumin by a squaraine dye. JAmChemSoc 2007;128:6024. [11] Loufty RO, Hsiao CK, Kazmaier PM. Photoconductivity of organic particle dispersions: squaraine dyes. Photogr Sci Eng 1983;27:5. [12] Merritt VY. Organic photovoltaic materials: squarylium and cyanine-TCNQ dyes. IBM J Res Dev 1978;22:353. [13] Piechowski AP, Bird GR, Morel DL, Stogryn EL. Desirable properties of photovoltaic dyes. J Phys Chem 1984;88:934. [14] Liang KN, Law KY, Whitten DG. Estimation of exciton sizes in squaraine monolayers by intralayer photoinduced electron transfer. J Phys Chem 1995;99:16704. [15] Chen CT, Marder SR, Cheng LT. Syntheses and linear and nonlinear optical properties of unsymmetrical squaraines with extended conjugation. J Am Chem Soc 1994;116:3117. [16] Ashwell GJ, Jefferies G, Hamilton DG, Lynch DE, Roberts MPS, Bahra GS, et al. Strong second-harmonic generation from centrosymmetric dyes. Nature 1995;375:385. [17] Ashwell GJ. A comment upon the aggregation of squaraine dyes. J Mater Chem 1998;8:373. [18] Johnson JR, Fu N, Arunkumar E, Leevy WM, Gammon ST, Worms DP, et al. Squaraine rotaxanes: superior substitutes for Cy-5 in molecular probes for near-infrared fluorescence cell imaging. Angew Chem Int Ed 2007;46:5528. [19] Oguz U, Akkaya EU. A squaraine-based sodium selective fluorescent chemosensor. Tetrahedron Lett 1998;39:5857. [20] Oguz U, Akkaya EU. One-pot synthesis of a red-fluorescent chemosensor from an azacrown, phloroglucinol and squaric acid: a simple in-solution construction of a functional molecular device. Tetrahedron Lett 1997;38:4509. [21] Akkaya EU, Turkyilmaz S. A squaraine-based near IR fluorescent chemosensor for calcium. Tetrahedron Lett 1997;38:4513. [22] Isgor YG, Akkaya EU. Chemosensing in deep red: a squaraine-based fluorescent chemosensor for pH. Tetrahedron Lett 1997;38:7417. [23] Thomas KG, Thomas KJ, Das S, George MV. A squaraine-based near-infrared absorbing sensor for the selective detection of transition and other metal ions in aqueous media. Chem Commun 1997:597. [24] Ros-Lis JV, Martı´nez-Ma´n˜ez R, Rurack K, Sanceno´n F, Soto J, Spieles M. Highly selective chromogenic signaling of Hg2þ in aqueous media at nanomolar levels employing a squaraine-based reporter. Inorg Chem 2004;43:5183. [25] Ros-Lis JV, Marcos MD, Martı´nez-Ma´n˜ez R, Rurack R, Soto J. A regenerative chemodosimeter based on metal-induced dye formation for the highly selective and sensitive optical determination of Hg2þ ions. Angew Chem Int Ed 2005;44:4405. [26] Jime´nez D, Martı´nez-Ma´n˜ez R, Sanceno´n F, Ros-Lis JV, Benito A, Soto J. A new chromo-chemodosimeter selective for sulfide anion. J Am Chem Soc 2003;125:9000. [27] Ros-Lis JV, Martine´z-Ma´n˜ez R, Soto J. A selective chromogenic reagent for cyanide determination. Chem Commun 2002:2248. [28] Ros-Lis JV, Garcı´a B, Jime´nez D, Martı´nez-Ma´n˜ez R, Sanceno´n F, Soto J, et al. Squaraines as fluorochromogenic probes for thiol-containing compounds and their application to the detection of biorelevant thiols. J Am Chem Soc 2004;126:4064. [29] Ros-Lis JV, Martı´nez-Ma´n˜ez R, Soto J. Colorimetric signaling of large aromatic hydrocarbons via the enhancement of aggregation processes. Org Lett 2005;7:2337. [30] Ajayaghosh A. Chemistry of squaraine-derived materials: near-IR dyes, low band gap systems, and cation sensors. Acc Chem Res 2005;38:449. [31] Snee PT, Somers RC, Nair G, Zimmer JP, Bawendi MG, Nocera DG. A ratiometric CdSe/ZnS nanocrystal pH sensor. J Am Chem Soc 2006;128:13320. [32] Arunkumar E, Ajayaghosh A, Daub J. Selective calcium ion sensing with a bichromophoric squaraine foldamer. J Am Chem Soc 2005;127:3156. [33] Balbo Block MA, Hecht S. Alternating (squarainereceptor) sensory polymers: modular one-pot synthesis and signal transduction via conformationally controlled exciton interaction. Macromolecules 2004;37:4761. [34] Chenthamarakshan CR, Ajayaghosh A. Enhanced sensitivity and selectivity in lithium ion recognition property of an oligomeric squaraine dye based fluorescent sensor. Tetrahedron Lett 1998;39:1795. [35] Thomas J, Sherman DB, Amiss TJ, Andaluz SA, Pitner JB. Synthesis and biosensor performance of a near-IR thiol-reactive fluorophore based on benzothiazolium squaraine. Bioconjug Chem 2007;18:1841. [36] Ajayaghosh A, Chithra P, Varghese R, Divya KP. Controlled self-assembly of squaraines to 1D supramolecular architectures with high molar absorptivity. Chem Commun 2008:969. [37] Jyothish K, Hariharan M, Ramaiah D. Chiral supramolecular assemblies of a squaraine dye in solution and thin films: concentration, temperature, and solvent-induced chirality inversion. Chem Eur J 2007;13:5944. [38] Hsueh SY, Lai CC, Liu YH, Peng SM, Chiu SH. Highly selective Naþ-templated formation of [2] Pseudorotaxanes exhibiting significant optical outputs. Angew Chem Int Ed 2007;46:2013. [39] Ajayaghosh A, Chithra P, Varghese R. Self-assembly of tripodal squaraines: cation-assisted expression of molecular chirality and change from spherical to helical morphology. Angew Chem Int Ed 2007;46:230. [40] Stoll RS, Severin N, Rabe JP, Hecht S. Synthesis of a novel chiral squaraine dye and its unique aggregation behavior in solution and in self-assembled monolayers. Adv Mater 2006;18:1271. [41] Bhattacharya S, Thomas M. Synthesis of a novel thiazole based dipeptide chemosensor for Cu(II) in water. Tetrahedron Lett 2000;41:10313. [42] Zheng Y, Orbulescu X, Ji X, Andreopoulos FM, Pham SM, Leblanc RM. Development of fluorescent film sensors for the detection of divalent copper. J Am Chem Soc 2003;125:2680. [43] Brasola E, Mancin F, Rampazzo E, Tecilla P, Tonellato U. A fluorescence nanosensor for Cu2þ on silica particles. Chem Commun 2003:3026. [44] Zheng Y, Cao X, Orbulescu J, Konka V, Antreopoulos FM, Pham SM, et al. Peptidyl fluorescent chemosensors for the detection of divalent copper. Anal Chem 2003;75:1706. [45] Kaur S, Kumar S. Photoactive chemosensors 4: a Cu2þ protein cavity mimicking fluorescent chemosensor for selective Cu2þ recognition. Tetrahedron Lett 2004;45:5081. [46] Kaur S, Kumar S. Photoactive chemosensors 3: a unique case of fluorescence enhancement with Cu(II). Chem Commun 2002:2840. [47] Kumar S, Kaur S, Singh G. Photoactive chemosensors 2: 8-hydroxyquinoline based Cu(II) selective fluorescent tripod. Supramol Chem 2003;15:65. [48] Kumar S, Pramilla Kaur S. Photoactive chemosensors. Part 1: a 9,10-anthraquinone and 2-aminothiophenol based Cu(II) selective chemosensor. Tetrahedron Lett 2002;43:1097. [49] Frausto da Silva JJR, Williams RJP. The biological chemistry of elements: the inorganic chemistry of life. Oxford: Clarendon Press; 1993. p. 388. [50] Sreejith S, Carol P, Chithra P, Ajayaghosh A. Squaraine dyes: a mine of molecular materials. J Mater Chem 2008;18:264. [51] BeverinaL,CrippaM,SaliceP,RuffoR,FerranteC, Fortunati I, et al. Indolic squaraines as two-photon absorbing dyes in the visible region: X-ray structure, electrochemical, and nonlinear optical characterization. ChemMater 2008;20:3242. [52] Bello KA, Ajayi JO. Near-infrared absorbing squarylium dyes. Dyes Pigments 1996;31:79. [53] Fabian J, Nakazumi H, Matsuoka M. Near-infrared absorbing dyes. Chem Rev 1992;92:1197. [54] Law KY. Squaraine chemistry. Absorption, fluorescence emission, and photophysics of unsymmetrical squaraines. J Phys Chem 1995;99:9818. [55] Sonawane ND, Rangnekar DW. Synthesis and application of 2-styryl-6,7- dichlorothiazolo[4,5-b]quinoxaline based fluorescent dyes: part 3. J Heterocycl Chem 2002;39:303. [56] Dailey S, Feas JW, Peace RJ, Sage IC, Till S, Wood EL. Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications. J Mater Chem 2001;11:2238. [57] Brien DO, Weaver MS, Lidzey DG, Bradley DDC. Use of poly(phenyl quinoxaline) as an electron transport material in polymer light-emitting diodes. Appl Phys Lett 1996;69:881. [58] Gazit A, App H, McMahon G, Chen J, Levitzki A, Bohmer FD. Tyrphostins. 5. Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: structureactivity relationships in quinoxalines, quinolines, and indole tyrphostins. J Med Chem 1996;39:2170. [59] Sehlstedt U, Aich P, Bergman J, Vallberg H, Norde B, Graslund A. Interactions of the antiviral quinoxaline derivative 9-OH-B220 {2,3-dimethyl-6-(dimethylaminoethyl)- 9-hydroxy-6H-indolo-[2,3-b]quinoxaline} with duplex and triplex forms of synthetic DNA and RNA. J Mol Biol 1998;278:31. [60] Basheer MC, Alex S, Thomas KG, Suresh CH, Das S. A squaraine-based chemosensor for Hg2þ and Pb2þ. Tetrahedron 2006;62:605. [61] Gloster DF, Cincotta L, Foley JW. Design, synthesis, and photophysical characterization of novel pentacyclic red shifted azine dyes. J Heterocycl Chem1999;36:25. [62] Cosmao JM, Collignon N, Queguiner G. Re´ duction alkylante de quelques compose´s he´ te´ roaromatiques polyazote´ s. J Heterocycl Chem 1979;16:973. [63] Mahajan SS, Nandre RG. Studies in the synthesis of 2-mercapto-5-methoxybenzimida zole. Indian J Chem Section B Org Chem 2006;45B(7):1756. [64] Ros-Lis JV, Martinex-Manez R, Sancenon F, Soto J, Spieles M, Rurack K. Squaraines as reporter units: insights into their photophysics, protonation and metal-ion coordination behaviour. Chem Eur J 2008;14:10101.
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited: 06 Jan 2010 07:12
Last Modified: 19 Sep 2010 05:41
URI: http://eprints.iisc.ernet.in/id/eprint/22276

Actions (login required)

View Item View Item