Abstract
Novel donor-π-acceptor dyes bearing the pyrimidine unit as an electron-withdrawing group have been synthesized by using combination of two processes, based on the microwave-assisted Suzuki cross-coupling reaction and nucleophilic aromatic substitution of hydrogen. Spectral properties of the obtained dyes in six aprotic solvents of various polarities have been studied by ultraviolet–visible and fluorescence spectroscopy. In contrast to the absorption spectra, fluorescence emission spectra displayed a strong dependence from their solvent polarities. The nature of the observed long wavelength maxima has been elucidated by means of quantum chemical calculations. The electrochemical properties of these dyes have been investigated by using cyclic voltammetry, while their photovoltaic performance was evaluated by a device fabrication study. The experimental and calculation data show that all of the dyes can be regarded as potentially good photosensitizers for dye-sensitized solar cells.
Similar content being viewed by others
References
Reichardt C, Welton T (2011) Solvents and solvent effects in organic chemistry. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Marini А, Muñoz-Losa А, Biancardi A, Mennucci B (2010) What is solvatochromism? J Phys Chem B 114:17128–17135
Reichardt C (1994) Solvatochromic dyes as solvent polarity indicators. Chem Rev 94:2319–2358
Bamfield P (2001) Chromic phenomena: technological application of colour chemistry. The Royal Society of Chemistry, Cambridge
Janzen MC, Ponder JB, Bailey DP, Ingison CK, Suslick KS (2006) Colorimetric sensor arrays for volatile organic compounds. Anal Chem 78(11):3591–3600
Anthonov VS, Hohla KL (1983) Dye stability under excimer-laser pumping. Appl Phys B 32(1):9–14
Speiser S, Shakkour N (1985) Photoquenching parameters for commonly used laser dyes. Appl Phys B 38(3):191–197
de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches. Chem Rev 97:1515–1566
Zhu LL, Li X, Ji FY, Ma X, Wang QC, Tian H (2009) Photolockable ratiometric viscosity sensitivity of cyclodextrine polypseudorotaxane with light-active rotor graft. Langmuir 25:3482–3486
Zhang D, Zhang Q, Su J, Tian H (2009) A dual-ion-switched molecular brake based on ferrocene. Chem Commun 1700–1702
Sansregret J, Drake JM, Thomas WRL, Lesiecki ML (1983) Light transport in planar luminescent solar concentrators: the role of DCM self-absorption. Appl Opt 22:573–577
Liu B, Zhu W, Zhang Q, Wu W, Xu M, Ning Z, Xie Y, Tian H (2009) Conveniently synthesized isophorone dyes for high efficiency dye-sensitized solar cell: tuning photovoltaic performance by structural modification of donor group in donor–π–acceptor system. Chem Commun :1766–1768
Verbitskiy EV, Cheprakova EM, Subbotina JO, Schepochkin AV, Slepukhin PA, Rusinov GL, Charushin VN, Chupakhin ON, Makarova NI, Metelitsa AV, Minkin VI (2014) Synthesis, spectral and electrochemical properties of pyrimidine-containing dyes as photosensitizers for dye-sensitized solar cells. Dyes Pigments 100:201–214
Zhang XH, Chen BJ, Lin XQ, Wong QTY, Lee CS, Kwong HL, Lee ST, Wu SK (2001) A new family of red dopants based on chromen-containing compounds for organic luminescent device. Chem Mater 13(5):1565–1569
Gompper R, Mair H-J, Polborn K (1997) Synthesis of oligo(diazaphenyls). Tailormade fluorescent heteroaromatics and pathways to nanostructures. Synthesis 696–708
Kanbara T, Kushida T, Saito N, Kuwajima I, Kubota K, Yamamoto T (1992) Preparation and properties of highly electron-accepting poly(pyrimidine2,5-diyl). Chem Lett 583–586
Wong K-T, Hung T-S, Lin Y, Wu C-C, Lee G-H, Peng S-M, Chou CH, Su YO (2002) Suzuki coupling approach for the synthesis of phenylene-pyrimidine alternating oligomers for blue light-emitting material. Org Lett 4(4):513–516
Achelle S, Ramodenc Y, Marsais F, Plé N (2008) Star- and banana-shaped oligomers with a pyrimidine core: synthesis and light-emitting properties. Eur J Org Chem 3129–3140
Ortiz RP, Casado J, Hernández V, López Navarrete JT, Letizia JA, Ratner MA, Facchetti A, Marks TJ (2009) Thiophene-diazine molecular semiconductors: synthesis, structural, electrochemical, optical, and electronic structural properties; implementation in organic field-effect transistors. Chem Eur J 15(20):5023–5039
Kojima T, Nishida J, Tokito S, Yamashita Y (2009) New n-type field-effect transistors based on pyrimidine-containing compounds with (trifluoromethyl) phenyl groups. Chem Lett 38:428–429
Achelle S, Plé N (2012) Pyrimidine ring as building block for the synthesis of functionalized π-conjugated materials. Curr Org Synth 9:163–187
Achelle S, Baudequin C (2013) Recent advances in pyrimidine derivatives as luminescent, photovoltaic and non-linear optical materials. Targets Heterocycl Syst 17:1–34
Itami K, Yamazaki D, Yoshida J (2004) Pyrimidine-core extended π-systems: general synthesis and interesting fluorescent properties. J Am Chem Soc 126:15396–15397
Bagley MC, Lin Z, Pope SJA (2009) Barium manganate in microwave-assisted oxidation reactions: synthesis of solvatochromic 2,4,6-triarylpyrimidines. Tetrahedron Lett 50:6818–6822
Tumkevičius S, Voitechovičius A, Adomėnas P (2012) Synthesis of novel 2,4,6-triarylpyrimidines. Chemija 23:61–67
Liu B, Hu XL, Liu J, Zhao YD, Huang ZL (2007) Synthesis and photophysical properties of novel pyrimidine-based two-photon absorption chromophores. Tetrahedron Lett 48:5958–5962
Li L, Ge J, Wu H, Xu QH, Yao SQ (2012) Organelle-specific detection of phosphatase activities with two-photon fluorogenic probes in cells and tissues. J Am Chem Soc 134:12157–12167
Achelle S, Malval JP, Aloïse S, Barsella A, Spangenberg A, Mager L, Akdas-Killig H, Fillaut JL, Caro B, Robin-le Guen F (2013) Synthesis, photophysics and nonlinear optical properties of stilbenoid pyrimidine-based dyes bearing methylenepyran donor groups. ChemPhysChem 14:2725–2736
Achelle S, Barsella A, Baudequin C, Caro B, Robin-le Guen F (2012) Synthesis and photophysical investigation of a series of push-pull arylvinyldiazine chromophores. J Org Chem 77:4087–4096
Castet F, Pic A, Champagne B (2014) Linear and nonlinear optical properties of arylvinyldiazine dyes: a theoretical investigation. Dyes Pigments 110:256–260
Denneval C, Achelle S, Baudequin C, Robin-le Guen F (2014) Prediction of photophysical properties of pyrimidine chromophores using Taguchi method. Dyes Pigments 110:49–55
Ling Q, Huang W, Mei Q, Weng J (2011) Preparation of 4-(hetero)-arylpyrimidins compounds as luminescent materials. Patent CN102206207
Weng J, Mei Q, Fan Q, Ling Q, Tong B, Huang W (2013) Bipolar luminescent materials containing pyrimidine terminals: synthesis, photophysical properties and a theoretical study. RSC Adv 3:21877–21887
Weng J, Mei Q, Ling Q, Huang W (2012) A new colorimetric and fluorescence ratiometric sensor for Hg2+ based on 4-pyren-1-yl-pyrimidine. Tetrahedron 68:3129–3134
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2013) he molecular orbital calculation was carried out using the gaussian 09, revision D.01. Gaussian, Wallingford
Yanai T, Tew D, Handy N (2014) A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem Phys Lett 393:51–57
Barone V, Cossi M (1998) Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model. J Phys Chem A 102(11):1995–2001
Improta R, Barone V, Scalmani G, Frisch MJ (2006) A state-specific polarizable continuum model time dependent density functional theory method for excited state calculations in solution. J Chem Phys 125:054103
Meech SR, Phillips D (1983) Photophysics of some common fluorescence standards. J Photochem 23:193–217
Barltrop JA, Coyle JD (1975) Excited states in organic chemistry. Wiley, London. New York, 376 p
Barich DH, Pugmire RJ, Grant DM (2001) Investigation of the structural conformation of biphenyl by solid state 13C NMR and quantum chemical NMR shift calculations. J Phys Chem A 105:6780–6784
Hadad C, Achelle S, Garcia-Martinez JC, Rodriguez-Lopez J (2011) 4-arylvinyl-2,6-di(pyridine-2-yl)pyrimidines: synthesis and optical properties. J Org Chem 76:3837–3845
Achelle S, Nouira I, Pfaffinger B, Ramondene Y, Ple N, Rodriguez-Lopez J (2009) V-shaped 4,6-Bis(arylvinyl)pyrimidine oligomers: synthesis and optical properties. J Org Chem 74:3711–3717
Ooyama Y, Nagano T, Inoue S, Imae I, Komaguchi K, Ohshita J, Harima Y (2011) Dye-sensitized solar cells based on donor-π-acceptor fluorescent dyes with a pyridine ring as an electron-withdrawing-injecting anchoring group. Chem Eur J 17:14837–14843
Ooyama Y, Inoue S, Nagano T, Kushimoto K, Ohshita J, Imae I, Komaguchi K, Harima Y (2011) Dye-sensitized solar cells based on donor-acceptor π-conjugated fluorescent dyes with a pyridine ring as an electron-withdrawing anchoring group. Angew Chem Int Ed 50:7429–7433
Ooyama Y, Harima Y (2012) Photophysical and electrochemical properties, and molecular structures of organic dyes for dye-sensitized solar cells. Chem Phys Chem 13:4032–4080
Ooyama Y, Yamaguchi N, Imae I, Komaguchi K, Ohshita J, Harima Y (2013) Dye-sensitized solar cells based on D-π-A fluorescent dyes with two pyridyl groups as an electronwithdrawing-injecting anchoring group. Chem Commun 49:2548–2550
Harima Y, Fujita T, Kano Y, Imae I, Komaguchi K, Ooyama Y, Ohshita J (2013) Lewis-acid sites of TiO2 surface for adsorption of organic dye having pyridyl group as anchoring unit. J Phys Chem C 117:16364–16370
Lu J, Xu X, Li Z, Cao K, Cui J, Zhang Y, Shen Y, Li Y, Zhu J, Dai S, Chen W, Cheng Y, Wang M (2013) Zinc porphyrins with a pyridine-ring-anchoring group for dye-sensitized solar cells. Chem Asian J 8:956–962
Ooyama Y, Hagiwara Y, Mizumo T, Harima Y, Ohshita J (2013) Photovoltaic performance of dye-sensitized solar cells based on D-π-A type BODIPY dye with two pyridyl groups. New J Chem 37:2479–2485
Cossi M, Barone V (2001) Time-dependent density functional theory for molecules in liquid solutions. J Chem Phys 115:4708–4717
Acknowledgments
This work was supported by the Russian Foundation for Basic Research (research projects No. 13-03-96049-r_ural_a, 13-03-12434 ofi_м2, 13-03-90606-Arm_a, 14-03-01017-А, 14-03-00479-А and 14-03-31040-mol_а, 13-03-12415), the Council on Grants at the President of the Russian Federation (Program of State Support for Leading Scientific Schools of the Russian Federation and Young Scientists, Grant MK-3939.2014.3). N.I. Makarova, I.V. Dorogan, A.V. Metelitsa and V.I. Minkin would like to acknowledge the financial support of absorption, fluorescence and quantum chemical studies from the Ministry of Education and Science of Russian Federation in the framework of the State Assignment for Research project № 1895.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
ESM 1
(DOC 12653 kb)
Rights and permissions
About this article
Cite this article
Verbitskiy, E.V., Schepochkin, A.V., Makarova, N.I. et al. Synthesis, Photophysical and Redox Properties of the D–π–A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety. J Fluoresc 25, 763–775 (2015). https://doi.org/10.1007/s10895-015-1565-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-015-1565-6