Dicyanovinyl End-Capped 9,10-Bis (Phenylethynyl) Anthracenes for Organic Solar Cells

Danel, Krzysztof S.; Michalski, Oskar; Usatenko, Zoryana; Sanetra, Jerzy; Nowak, Elżbieta M.

doi:10.4467/2353737XCT.18.004.7955

Abstract

A series of 9,10-bis(phenylethynyl)anthracene dicyanovinyl end-capped derivatives have been used in bulk heterojunction (BHJ) photovoltaic cells prepared by the solution process. The compounds were excessively decorated with moieties enhancing solubility to avoid spontaneous crystallisations in the blends. The topology of the dyes is of the acceptor-donor-acceptor (A-D-A) type. The quantum chemical calculations were done at the B3LYP/6-31G(d) level of theory and HOMO-LUMO levels were calculated. The solar cells’ configuration was as follows: ITO/PEDOT:PSS/P3HT(P3OT)dyes/Al and parameters characterising them, open-circuit voltage (Voc), short-circuit current density (Jsc), fill factor (FF) and power conversion efficiency (PCE) are presented. Anthracene based A-D-A molecules showed photovoltaic activity with an average power conversion efficiencies (PCE) of 2.7%.

References

[1] Pope M., Kallmann H.P, Magnante P., Electroluminescence in Organic Crystals, J. Chem. Phys. 38, 1963, 2042–2046.10.1063/1.1733929
Search in Google Scholar Back to article
[2] Helfrich W., Schneider W.G., Recombination Radiation in Anthracene Crystals, Phys. Rev. Lett. 14, 1965, 229–231.10.1103/PhysRevLett.14.229
Search in Google Scholar Back to article
[3] Nasu K., Nakagawa T., Nomura H., Lin C.-J., Cheng C.-H., Tseng M.-R., Yasuda T., Adachi C., A highly luminescent spiro-anthracenone-based organic light-emitting diode exhibiting thermally activated delayed fluorescence, Chem. Commun. 49, 2013, 10385–10387.10.1039/C3CC44179B
Search in Google Scholar Back to article
[4] Wan W., Du H., Wang J., Le Y., Jiang H., Chen H., Zhu S., Hao J.A., Novel blue luminescent materials for organic light-emitting diodes based on C9-fluorenyl anthracenes, Dyes Pigm. 96, 2013, 642–652.10.1016/j.dyepig.2012.10.013
Search in Google Scholar Back to article
[5] Zhang P., Dou W., Ju Z., Yang L., Tang X., Liu W., Wu Y., A 9,9′-bianthracene-cored molecule enjoying twisted intramolecular charge transfer to enhance radiative-excitons generation for highly efficient deep-blue OLEDs, Org. Electron. 14, 2013, 915–925.10.1016/j.orgel.2012.12.040
Search in Google Scholar Back to article
[6] Wang J.-J., Hu T.-L., Bu X.-H., Cadmium(ii) and zinc(ii) metal-organic frameworks with anthracene-based dicarboxylic ligands: Solvothermal synthesis, crystal structures, and luminescent properties, CrystEngComm. 13, 2011, 5152–5161.10.1039/c1ce05287j
Search in Google Scholar Back to article
[7] Zhu M., Wang Q., Gu Y., Cao X., Zhong C., Ma D., Qin J., Yang C., Efficient deep-blue emitters comprised of an anthracene core and terminal bifunctional groups for nondoped electroluminescence, J. Mater. Chem. 21, 2011, 6409–6415.10.1039/c1jm10465a
Search in Google Scholar Back to article
[8] Zhang J., Xu B., Chen J., Ma S., Dong Y., Wang I., Li B., Ye L., Tian W., An organic luminescent molecule: What will happen when the “butterflies” come together?, Adv. Mater. 26, 2014, 739–745.10.1002/adma.201303639
Search in Google Scholar Back to article
[9] Ye S., Chen J., Di C.-A., Liu Y., Lu K., Wu W., Du C., Liu Y., Shuai Z., Yu G., Phenyl-substituted fluorene-dimer cored anthracene derivatives: Highly fluorescent and stable materials for high performance organic blue- and white-light-emitting diodes, J. Mater. Chem. 20, 2010, 3186–3194.10.1039/b925418h
Search in Google Scholar Back to article
[10] Li B., Miao W., Cheng L., Synthesis and fluorescence properties of 9,10-bis(phenylethynyl) anthracences, Dyes Pigm. 43, 1999, 161–165.10.1016/S0143-7208(99)00057-1
Search in Google Scholar Back to article
[11] Kilså K., Macpherson A.N., Gillbro T., Mårtensson J., Albinsson B., Control of electron transfer in supramolecular systems, Spectrochim. Acta, Part A 57, 2001, 2213–2227.10.1016/S1386-1425(01)00497-8
Search in Google Scholar Back to article
[12] Kawai T., Sasakia T., Irie M., A photoresponsive laser dye containing photochromic dithienylethene units, Chem. Commun., 2001, 711–712.10.1039/b100330p
Search in Google Scholar Back to article
[13] Kilså K., Kajanus J., Macpherson A.N., Mårtensson J., Albinsson B., Bridge-Dependent Electron Transfer in Porphyrin-Based Donor-Bridge-Acceptor Systems, J. Am. Chem. Soc. 123, 2001, 3069–3080.10.1021/ja003820k11457018
Search in Google Scholar Back to article
[14] Ribierre J.C., Ruseckas A., Cavaye H., Barcena H.S., Burn P.L., Samuel I.D.W., Photophysical Properties of 9,10-Disubstituted Anthracene Derivatives in Solution and Films, J. Phys. Chem. A 115, 2011, 7401–7405.10.1021/jp200668x21574639
Search in Google Scholar Back to article
[15] Levitus M., Garcia-Garibay M.A., Polarized Electronic Spectroscopy and Photophysical Properties of 9,10-Bis(phenylethynyl)anthracene, J. Phys. Chem. A 104, 2000, 8632–8637.10.1021/jp001483w
Search in Google Scholar Back to article
[16] Angelova A., Ionov R., Monolayer and Spectroscopic Studies of an Amphiphilic (Phenylethynyl)anthracene Probe in Pure and Mixed Films with Charged and Neutral Lipids, Langmuir 15, 1999, 7199–7207.10.1021/la981536p
Search in Google Scholar Back to article
[17] Angelov B., Angelova A., Ionov R., An Amino-Substituted Phenylethynyl-anthracene Probe Shows a Sensitivity to Changes in the Lipid Monolayer Curvature of Nonlamellar Lipid/ Water Phases, J. Phys. Chem. B 104, 2000, 9140–9148.10.1021/jp993779b
Search in Google Scholar Back to article
[18] Lübtow M., Helmers I., Stepanenko V., Albuquerque R.Q., Marder T.B., Fernández G., Self-Assembly of 9,10-Bis(phenylethynyl) Anthracene (BPEA) Derivatives: Influence of p–p and Hydrogen-Bonding Interactions on Aggregate Morphology and Self-Assembly Mechanism, Chem. Eur. J. 23, 2017, 6198–6205.10.1002/chem.20160598928187239
Search in Google Scholar Back to article
[19] Wang C.-Y., Ediger M.D., Enhanced Translational Diffusion of 9,10-Bis(phenylethynyl) anthracene (BPEA) in Polystyrene, Macromolecules 30, 1997, 4770–4771.10.1021/ma961907d
Search in Google Scholar Back to article
[20] Deppe D.D., Dhinojwala A., Torkelson J.M., Small Molecule Probe Diffusion in Thin Polymer Films Near the Glass Transition: A Novel Approach Using Fluorescence Nonradiative Energy Transfer, Macromolecules 29, 1996, 3898–3908.10.1021/ma960024j
Search in Google Scholar Back to article
[21] Wisnudel M.B., Torkelson J.M., Small-Molecule Probe Diffusion in Polymer Solutions: Studies by Taylor Dispersion and Phosphorescence Quenching, Macromolecules 29, 1996, 6193–6207.10.1021/ma960635b
Search in Google Scholar Back to article
[22] Giménez R., Pinol M., Serrano J. L., Luminescent Liquid Crystals Derived from 9,10-Bis(Phenylethynyl)anthracene, Chem. Mater. 16, 2004, 1377–1383.10.1021/cm030582u
Search in Google Scholar Back to article
[23] Xiao D., Xian Y., Liu L., Gu Z., Wen B., Organic nanoparticle of 9,10-Bis(phenylethynyl) anthracene: a novel electrochemiluminescence emitter for sensory detection of amines, New J. Chem. 37, 2013, 1–3.10.1039/c3nj01227a
Search in Google Scholar Back to article
[24] Ponnu A., Anslyn E.V., A fluorescence-based cyclodextrin sensor to detect nitroaromatic explosives, Supramol. Chem. 22, 2010, 65–71.10.1080/10610270903378032
Search in Google Scholar Back to article
[25] Kim S.-O., Lee M.W., Jang S.H., Park S.M., Park J. W., Park M.-H., Kang S.H., Kim Y.-H., Song C.K., Kwon S.K., Organic semiconductor based on phenylethynyl end-capped anthracene, Thin Solid Films 519, 2011, 7998–8002.10.1016/j.tsf.2011.05.060
Search in Google Scholar Back to article
[26] Li Y., Ji D., Liu J., Yao Y., Fu X., Zhu W., Xu Ch., Dong H., Li J., Hu W., Quick Fabrication of Large-area Organic Semiconductor Single Crystal Arrays with a Rapid Annealing Self-Solution-Shearing Method, Sci. Rep. 5, 2015, 13195,1–9.10.1038/srep13195
Search in Google Scholar Back to article
[27] Malakhov A.D., Skorobogatyi M.V., Prokhorenko I.A., Gontarev S.V., Kozhich D.T., Stetsenko A.D., Stepanova I.A., Shenkarev Z.O., Berlin Y.A., Korshun V.A., 1-(Phenylethynyl) pyrene and 9,10-Bis(phenylethynyl)anthracene, Useful Fluorescent Dyes for DNA Labeling: Excimer Formation and Energy Transfer, Eur. J. Org. Chem., 2004, 1298–1307.10.1002/ejoc.200300677
Search in Google Scholar Back to article
[28] Fatemi D.J., Murata H., Merritt C.D., Kafafi Z.H., Highly Fluorescent Molecular Organic Composites for Light-Emitting Diodes, Synth. Met. 85, 1997, 1225–1228.10.1016/S0379-6779(97)80215-9
Search in Google Scholar Back to article
[29] Huang J., Su J.-H., Tian H., The development of anthracene derivatives for organic light-emitting diodes, J. Mater. Chem. 22, 2012, 10977–10989.10.1039/c2jm16855c
Search in Google Scholar Back to article
[30] Fitzner R., Mena-Osteritz E., Walzer K., Pfeiffer M., Bäuerle P., A–D–A-Type Oligothiophenes for Small Molecule Organic Solar Cells: Extending the π-System by Introduction of Ring-Locked Double Bonds, Adv. Funct. Mater. 25, 2015, 1845–1856.10.1002/adfm.201404210
Search in Google Scholar Back to article
[31] Lai Y.-Y., Yeh J.-M., Tsai C.-E., Cheng Y.-J., Synthesis, Molecular and Photovoltaic Properties of an Indolo[3,2-b]indole- Based Acceptor–Donor–Acceptor Small Molecule, Eur. J. Org. Chem., 2013, 5076–5084.10.1002/ejoc.201300443
Search in Google Scholar Back to article
[32] Sahu D., Padhy H., Patra D., Yin J.-F., Hsu Y.-C., Lin J. T., Lu K.-L., Wei K.-H., Lin H.-C., Synthesis and applications of novel acceptoredonoreacceptor organic dyes with dithienopyrroleand fluorene-cores for dye-sensitized solar cells, Tetrahedron 67, 2011, 303–311.10.1016/j.tet.2010.11.044
Search in Google Scholar Back to article
[33] Kuropatov V., Klementieva S., Fukin G., Mitin A., Ketkov S., Budnikova Y., Cherkasov V., Abakumov G., Novel method for the synthesis of functionalized tetrathiafulvalenes, an acceptoredonoreacceptor molecule comprising of two o-quinone moieties linked by a TTF bridge, Tetrahedron 66, 2010, 7605–7611.10.1016/j.tet.2010.07.038
Search in Google Scholar Back to article
[34] Silvestri F., Marrocchi A., Acetylene-Based Materials in Organic Photovoltaics, Int. J. Mol. Sci. 11, 2010, 1471–1508.10.3390/ijms11041471
Search in Google Scholar Back to article
[35] Danel K., Lin J.T., Novel red-light-emitting 9,10-bis(phenylethynyl)anthracenes, Arkivoc (i), 2002, 12–18.10.3998/ark.5550190.0003.103
Search in Google Scholar Back to article
[36] Danel K., Ozga K., Kityk I.V., Circularly light-induced electrogyration in the arylethynyl derivatives incorporated within the oligoetheracrylate photopolymer matrices, Chem. Phys. 313, 2005, 33–38.10.1016/j.chemphys.2004.12.015
Search in Google Scholar Back to article
[37] Frisch M.J., Trucks G.W., Schlegel H.B. et al., Gaussian 03: Revision E.01, Gaussian Inc., Wallingford CT 2004.
Search in Google Scholar Back to article
[38] Fudickar W., Linker T., Why Triple Bonds Protect Acenes from Oxidation and Decomposition, J. Am. Chem. Soc. 134, 2012, 15071–15082.10.1021/ja306056x
Search in Google Scholar Back to article
[39] Yucel B., Meral K., Ekinci D., Uzunoğlu G.Y., Tüzün N.S., Özbey S., Kazak C., Ozdemir Y., Sanli B., Kayık G., Dağdeviren M., Synthesis and characterization of solution processable 6,11-dialkynyl substituted indeno[1,2-b]anthracenes, Dyes Pigm. 100, 2014, 104–117.10.1016/j.dyepig.2013.08.024
Search in Google Scholar Back to article
[40] Pettersson L.A.A., Ghosh S., Inganas O., Optical anisotropy in thin films of poly (3,4-ethylenedioxythiophene)–poly(4-styrenesulfonate), Org. Electron. 3, 2002, 143–148.10.1016/S1566-1199(02)00051-4
Search in Google Scholar Back to article
[41] Fujiwara H., Spectroscopic Ellipsometry: Principles and Applications, John Wiley&Sons, Ltd. 2007.10.1002/9780470060193
Search in Google Scholar Back to article
[42] Feller L., Bearinger J.P., Wu L., Hubbell J. A., Textor M., Tosatti S., Micropatterning of gold substrates based on poly(propylene sulfide-bl-ethylene glycol), (PPS–PEG) background passivation and the molecular-assembly patterning by lift-off (MAPL) technique, Surf. Sci. 602, 2008, 2305–2310.10.1016/j.susc.2008.05.010261053519578480
Search in Google Scholar Back to article
[43] Woollam J. A., Co. Inc.CopleteEASETM Data Analysis Manual, Lincon 2009.
Search in Google Scholar Back to article
[44] Bujak P., Kulszewicz-Bajer I., Zagorska M., Maurel V., Wielgus I., Pron A., Polymers for Electronics and Spintronics, Chem. Soc. Rev. 42, 2013, 8895–8999.10.1039/c3cs60257e24030727
Search in Google Scholar Back to article
[45] Bijak K., Sek D., Siwy M., Grucela-Zajac M., Janeczek H., Wiacek M., Malecki G., Schab-Balcerzak E., Spectral, electrochemical and thermal characteristics of glass forming hydrazine derivatives, Opt. Mater. 37, 2014, 498–510.10.1016/j.optmat.2014.07.013
Search in Google Scholar Back to article
[46] Kung Y.-C., Hsiao S.-H., Novel luminescent and electrochromic polyhydrazides and polyoxadiazoles bearing pyrenylamine moieties, Polym. Chem. 2, 2011, 1720–1727.10.1039/c1py00115a
Search in Google Scholar Back to article
[47] Grigoras M., Vacareanu L., Ivan T., Catargiu A.M., Photophysical properties of isoelectronic oligomers with vinylene, imine, azine and ethynylene spacers bearing triphenylamine and carbazole end-groups, Dyes Pigm. 98, 2013, 71–81.10.1016/j.dyepig.2013.01.025
Search in Google Scholar Back to article
[48] Mishra A., Bäuerle P., Small Molecule Organic Semiconductors on the Move: Promises for Future Solar Energy Technology, Angew. Chem. Int. Ed. 51, 2012, 2020–2067.10.1002/anie.20110232622344682
Search in Google Scholar Back to article

Dicyanovinyl End-Capped 9,10-Bis (Phenylethynyl) Anthracenes for Organic Solar Cells

Abstract

Paradigm

My account