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Journal of Materials Science: Materials in Electronics
Erschienen in: Journal of Materials Science: Materials in Electronics 12/2017

01.03.2017

Effects of donor position on dibenzofulvene-based organic dyes for photovoltaics

verfasst von: Giuseppina Anna Corrente, Eduardo Fabiano, Luisa De Marco, Gianluca Accorsi, Roberto Giannuzzi, Antonio Cardone, Giuseppe Gigli, Giuseppe Ciccarella, Agostina-Lina Capodilupo

Erschienen in: Journal of Materials Science: Materials in Electronics | Ausgabe 12/2017

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Abstract

A series of push–pull organic dyes based on the cyanoacrylic acid as the acceptor/anchoring group, a dibenzofulvene (DBF) connected with thienyl rings as the π-bridge, and donor units linked to different positions of the DBF molecule were synthetized and studied. The effects of the donor position on optical and photovoltaic properties were investigated through photophysics, electrochemical and photovoltaic measurements. The results uphold photovoltaic performances largely depend on the electronic structure of the dyes with a synergistic interaction between donor and acceptor groups. In detail, a fine tuning of the photophysical properties can be reached simply selecting the position of the donor unit on the DBF molecule. In particular, the dyes bearing the donor unit on the 3,6-positions of the DBF show better performances in term of light absorption and cell efficiency with respect to the dyes with the donor unit on the 2,7-positions.
Vorheriger Artikel Microwave—assisted hydrothermal synthesis of monoclinic bismuth trioxide nanorods: optical and photocatalytic properties
Nächster Artikel MOVPE growth of InAsBi/InAs/GaAs heterostructure analyzed by in situ spectral reflectance

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Literatur
1.
A.C. Arias, J.D. MacKenzie, I. McCulloch, J. Rivnay, A. Salleo, Materials and applications for large area electronics: solution-based approaches. Chem. Rev. 110, 3–24 (2010)CrossRef
2.
S. Achelle, A. Barsella, B. Caro, F. Robin-le Guen, Donor-linker-acceptor (D-[small pi]-A) diazine chromophores with extended [small pi]-conjugated cores: synthesis, photophysical and second order nonlinear optical properties. RSC Adv. 5, 39218–39227 (2015)CrossRef
3.
M. Sarma, T. Chatterjee, S. Ghanta, S.K. Das, D-π-A-A-π-D Prototype 2,2′-bipyridine dyads exhibiting large structure and environment-sensitive fluorescence: synthesis, photophysics, and computation. J. Org. Chem. 77, 432–444 (2012)CrossRef
4.
H. Moon, W.S. Jahng, M.D. Curtis, Transistor performance of a “push-pull”, [small pi]-stacked bithiazole-ethylenedioxythiophene co-oligomer. J. Mater. Chem. 18, 4856–4863 (2008)CrossRef
5.
T. Kimoto, K. Tanaka, M. Kawahata, K. Yamaguchi, S. Otsubo, Y. Sakai, Y. Ono, A. Ohno, K. Kobayashi, Bis(methylthio)tetracenes: synthesis, crystal-packing structures, and OFET properties. J. Org. Chem. 76, 5018–5025 (2011)CrossRef
6.
D. Yu, Y. Liu, M. Xiao, Q. Fan, W. Su, X. Li, H. Tan, Y. Wang, R. Yang, W. Zhu, Synthesis and photovoltaic performance of DPP-based small molecules with tunable energy levels by altering the molecular terminals. Dyes Pigm. 125, 151–158 (2016)CrossRef
7.
A.L. Capodilupo, E. Fabiano, L. De Marco, G. Ciccarella, G. Gigli, C. Martinelli, A. Cardone, [1]Benzothieno[3,2-b]benzothiophene-based organic dyes for dye-sensitized solar cells. J. Org. Chem. 81, 3235–3245 (2016)CrossRef
8.
J.L. Segura, N. Martin, D.M. Guldi, Materials for organic solar cells: the C60/[small pi]-conjugated oligomer approach. Chem. Soc. Rev. 34, 31–47 (2005)CrossRef
9.
Z. Wang, M. Liang, Y. Tan, L. Ouyang, Z. Sun, S. Xue, Organic dyes containing dithieno[2,3-d:2[prime or minute],3[prime or minute]-d[prime or minute]]thieno[3,2-b:3[prime or minute],2[prime or minute]-b[prime or minute]]dipyrrole core for efficient dye-sensitized solar cells. J. Mater. Chem. A 3, 4865–4874 (2015)CrossRef
10.
C. Baldoli, S. Bertuolo, E. Licandro, L. Viglianti, P. Mussini, G. Marotta, P. Salvatori, F. De Angelis, P. Manca, N. Manfredi, A. Abbotto, Benzodithiophene based organic dyes for DSSC: effect of alkyl chain substitution on dye efficiency. Dyes Pigm. 121, 351–362 (2015)CrossRef
11.
Q. Qi, X. Wang, L. Fan, B. Zheng, W. Zeng, J. Luo, K.-W. Huang, Q. Wang, J. Wu, N-annulated perylene-based push–pull-type sensitizers. Org. Lett. 17, 724–727 (2015)CrossRef
12.
A. Scrascia, L. De Marco, S. Laricchia, R.A. Picca, C. Carlucci, E. Fabiano, A.L. Capodilupo, F. Della Sala, G. Gigli, G. Ciccarella. Fluorine-thiophene-substituted organic dyes for dye sensitized solar cells. J. Mater. Chem. A 1, 11909–11921 (2013)CrossRef
13.
S.F. Völker, M. Renz, M. Kaupp, C. Lambert, Squaraine dyes as efficient coupling bridges between triarylamine redox centres.Chemistry 17 14147–14163 (2011)CrossRef
14.
Z. Li, Y. Zang, C.-C. Chueh, N. Cho, J. Lu, X. Wang, J. Huang, C.-Z. Li, J. Yu, A.K.Y. Jen, Tetrathienodibenzocarbazole based donor–acceptor type wide band-gap copolymers for polymer solar cell applications. Macromolecules 47, 7407–7415 (2014)CrossRef
15.
M. Velusamy, K.R. Justin Thomas, J.T. Lin, Y.-C. Hsu, K.-C. Ho, Organic dyes incorporating low-band-gap chromophores for dye-sensitized solar cells. Org. Lett. 7, 1899–1902 (2005)CrossRef
16.
Y. Wu, W.-H. Zhu, S.M. Zakeeruddin, M. Grätzel, Insight into D–A–π–A structured sensitizers: a promising route to highly efficient and stable dye-sensitized solar cells. ACS Appl. Mater. Interfaces 7, 9307–9318 (2015)CrossRef
17.
H. Zhao, J. Long, X. Luo, B. Zhao, S. Tan, 2-Ethynyl-6-methylthieno[3,2-b]thiophene as an efficient π spacer for porphyrin-based dyes. Dyes Pigm. 122, 168–176 (2015)CrossRef
18.
Y. Wu, W. Zhu, Organic sensitizers from D-[small pi]-A to D-A-[small pi]-A: effect of the internal electron-withdrawing units on molecular absorption, energy levels and photovoltaic performances. Chem. Soc. Rev. 42, 2039–2058 (2013)CrossRef
19.
S.C. Rasmussen, R.L. Schwiderski, M.E. Mulholland, Thieno[3,4-b]pyrazines and their applications to low band gap organic materials. Chem. Commun. (Camb.) 47, 11394–11410 (2011)CrossRef
20.
D. Jariwala, V.K. Sangwan, L.J. Lauhon, T.J. Marks, M.C. Hersam, Carbon nanomaterials for electronics, optoelectronics, photovoltaics, and sensing. Chem. Soc. Rev. 42, 2824–2860 (2013)CrossRef
21.
L. Pandey, C. Risko, J.E. Norton, J.-L. Brédas, Donor–acceptor copolymers of relevance for organic photovoltaics: a theoretical investigation of the impact of chemical structure modifications on the electronic and optical properties. Macromolecules 45, 6405–6414 (2012)CrossRef
22.
M. Liang, J. Chen, Arylamine organic dyes for dye-sensitized solar cells. Chem. Soc. Rev. 42, 3453–3488 (2013)CrossRef
23.
A. Bessette, G.S. Hanan, Design, synthesis and photophysical studies of dipyrromethene-based materials: insights into their applications in organic photovoltaic devices. Chem. Soc. Rev. 43, 3342–3405 (2014)CrossRef
24.
B. Yao, X. Ye, J. Zhang, X. Wan, Electrochromism of a fused acceptor–donor–acceptor triad covering entire UV–vis and near-infrared regions. Org. Lett. 16, 5378–5381 (2014)CrossRef
25.
A. Heckmann, C. Lambert, M. Goebel, R. Wortmann Synthesis and photophysics of a neutral organic mixed-valence compound. Angew. Chem. Int. Ed. 43, 5851–5856 (2004)CrossRef
26.
A.L. Capodilupo, L. De Marco, E. Fabiano, R. Giannuzzi, A. Scrascia, C. Carlucci, G.A. Corrente, M.P. Cipolla, G. Gigli, G. Ciccarella, New organic dyes based on a dibenzofulvene bridge for highly efficient dye-sensitized solar cells. J. Mater. Chem. A 2, 14181–14188 (2014)CrossRef
27.
A.L. Capodilupo, L. De Marco, G.A. Corrente, R. Giannuzzi, E. Fabiano, A. Cardone, G. Gigli, G. Ciccarella, Synthesis and characterization of a new series of dibenzofulvene based organic dyes for DSSCs. Dyes Pigm. 130, 79–89 (2016)CrossRef
28.
F. Lincker, B. Heinrich, R. De Bettignies, P. Rannou, J. Pecaut, B. Grevin, A. Pron, B. Donnio, R. Demadrille, Fluorenone core donor-acceptor-donor [small pi]-conjugated molecules end-capped with dendritic oligo(thiophene)s: synthesis, liquid crystalline behaviour, and photovoltaic applications. J. Mater. Chem. 21, 5238–5247 (2011)CrossRef
29.
K.R. Baheti, C.-P. Justin Thomas, C.-T. Lee, K.-C. Li, Ho, Organic dyes containing fluoren-9-ylidene chromophores for efficient dye-sensitized solar cells. J. Mater. Chem. A 2, 5766–5779 (2014)CrossRef
30.
S. Karak, P.J. Homnick, L.A. Renna, D. Venkataraman, J.T. Mague, P.M. Lahti, Solution-processed photovoltaics with a 3,6-Bis(diarylamino)fluoren-9-ylidene Malononitrile. ACS Appl. Mater. Interfaces 6, 16476–16480 (2014)CrossRef
31.
J. Kim, S.H. Kim, I.H. Jung, E. Jeong, Y. Xia, S. Cho, I.-W. Hwang, K. Lee, H. Suh, H.-K. Shim, H.Y. Woo, Synthesis and characterization of indeno[1,2-b]fluorene-based low bandgap copolymers for photovoltaic cells. J. Mater. Chem. 20, 1577–1586 (2010)CrossRef
32.
N. Delbosc, W.Z.N. Yahya, N. Lemaitre, S. Berson, F. Fuchs, B. Grevin, J. Faure-Vincent, J.-P. Travers, R. Demadrille, Synthesis, optoelectronic and photovoltaic properties of conjugated alternating copolymers incorporating 2,1,3-benzothiadiazole or fluorenone units: a comparative study. RSC Adv. 4, 15236–15244 (2014)CrossRef
33.
C.-H. Siu, L.T. Lin Lee, P.-Y. Ho, P. Majumdar, C.-L. Ho, T. Chen, J. Zhao, H. Li, W.-Y. Wong, Fluorene-bridged organic dyes with di-anchoring groups for efficient co-adsorbent-free dye-sensitized solar cells. J. Mater. Chem. C 2, 7086–7095 (2014)CrossRef
34.
N.S. Hush, Distance dependence of electron transfer rates. Coord. Chem. Rev. 64, 135–157 (1985)CrossRef
35.
M. Gholami, R.R. Tykwinski, Oligomeric and polymeric systems with a cross-conjugated π-framework. Chem. Rev. 106, 4997–5027 (2006)CrossRef
36.
J.-J. Shen, J.-Y. Shao, X. Zhu, Y.-W. Zhong, Amine–Amine electronic coupling through a dibenzo[a,e]pentalene bridge. Org. Lett. 18, 256–259 (2016)CrossRef
37.
L.A. Estrada, J.E. Yarnell, D.C. Neckers, Revisiting fluorenone photophysics via dipolar fluorenone derivatives. J. Phys. Chem. A 115, 6366–6375 (2011)CrossRef
38.
L.A. Estrada, X. Cai, D.C. Neckers, Nonradiative decay mechanism of fluoren-9-ylidene malononitrile ambipolar derivatives. J. Phys. Chem. A 115, 2184–2195 (2011)CrossRef
39.
L.A. Estrada, D.C. Neckers, Synthesis and photophysics of ambipolar fluoren-9-ylidene malononitrile derivatives. J. Org. Chem. 74, 8484–8487 (2009)CrossRef
40.
G.L. Eakins, J.S. Alford, B.J. Tiegs, B.E. Breyfogle, C.J. Stearman, Tuning HOMO–LUMO levels: trends leading to the design of 9-fluorenone scaffolds with predictable electronic and optoelectronic properties. J. Phys. Org. Chem. 24, 1119–1128 (2011)CrossRef
41.
M. Shigeta, M. Morita, G.-I. Konishi, Selective formation of twisted intramolecular charge transfer and excimer emissions on 2,7-bis(4-Diethylaminophenyl)-fluorenone by choice of solvent. Molecules 17, 4452 (2012)CrossRef
42.
P.J. Homnick, P.M. Lahti, Modular electron donor group tuning of frontier energy levels in diarylaminofluorenone push-pull molecules. Phys. Chem. Chem. Phys. 14, 11961–11968 (2012)CrossRef
43.
P.J. Homnick, J.S. Tinkham, R. Devaughn, P.M. Lahti, Engineering frontier energy levels in donor–acceptor fluoren-9-ylidene malononitriles versus fluorenones. J. Phys. Chem. A 118, 475–486 (2014)CrossRef
44.
G.A. Crosby, J.N. Demas, Measurement of photoluminescence quantum yields. Review. J. Phys. Chem. 75, 991–1024 (1971)CrossRef
45.
K. Nakamaru, Synthesis, luminescence quantum yields, and lifetimes of trischelated ruthenium(ii) mixed-ligand complexes including 3,3′-dimethyl-2,2′-bipyridyl. Bull. Chem. Soc. Jpn. 55, 2697–2705 (1982)CrossRef
46.
L.A. Constantin, E. Fabiano, F. Della Sala, Meta-GGA exchange-correlation functional with a balanced treatment of nonlocality. J. Chem. Theory Comput. 9, 2256–2263 (2013)CrossRef
47.
D.H. Evans, One-electron and two-electron transfers in electrochemistry and homogeneous solution reactions. Chem. Rev. 108, 2113–2144 (2008)CrossRef
48.
S. Pluczyk, P. Zassowski, C. Quinton, P. Audebert, V. Alain-Rizzo, M. Lapkowski, Unusual electrochemical properties of the electropolymerized thin layer based on a s-tetrazine-triphenylamine monomer. J. Phys. Chem. C 120, 4382–4391 (2016)CrossRef
49.
A.D. Becke, A new mixing of Hartree–Fock and local density-functional theories. J. Chem. Phys. 98, 1372–1377 (1993)CrossRef
50.
Y. Zhao, D.G. Truhlar, The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor. Chem. Acc. 120, 215–241 (2008)CrossRef
51.
R. Li, J. Zheng, D.G. Truhlar, Density functional approximations for charge transfer excitations with intermediate spatial overlap. Phys. Chem. Chem. Phys. 12, 12697–12701 (2010)CrossRef
52.
M. Pastore, E. Mosconi, F. De Angelis, M. Grätzel, A computational investigation of organic dyes for dye-sensitized solar cells: benchmark, strategies, and open issues. J. Phys. Chem. C 114, 7205–7212 (2010)CrossRef
53.
S. Kupfer, J. Guthmuller, L. González, An assessment of RASSCF and TDDFT energies and gradients on an organic donor–acceptor dye assisted by resonance raman spectroscopy. J. Chem. Theory Comput. 9, 543–554 (2013)CrossRef
54.
G. Garcia, C. Adamo, I. Ciofini, Evaluating push-pull dye efficiency using TD-DFT and charge transfer indices. Phys. Chem. Chem. Phys. 15, 20210–20219 (2013)CrossRef
55.
E. Gabrielle, J.-P. Gomez, Korb, probing rubber cross-linking generation of industrial polymer networks at nanometer scale. J. Phys. Chem. B 120, 5581–5589 (2016)CrossRef
56.
F. Weigend, M. Häser, H. Patzelt, R. Ahlrichs, RI-MP2: optimized auxiliary basis sets and demonstration of efficiency. Chem. Phys. Lett. 294, 143–152 (1998)CrossRef
57.
G. Klamt, G. Schuurmann COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc. Perkin Trans. 2, 799–805 (1993)CrossRef
58.
A. Klamt, V. Jonas, Treatment of the outlying charge in continuum solvation models. J. Chem. Phys. 105, 9972–9981 (1996)CrossRef
59.
60.
G. Lambert, J. Noll, J. Schelter, Bridge-mediated hopping or superexchange electron-transfer processes in bis(triarylamine) systems. Nat Mater 1, 69–73 (2002)CrossRef
61.
A.L. Capodilupo, V. Vergaro, E. Fabiano, M. De Giorgi, F. Baldassarre, A. Cardone, A. Maggiore, V. Maiorano, D. Sanvitto, G. Gigli, G. Ciccarella, Design and synthesis of fluorenone-based dyes: two-photon excited fluorescent probes for imaging of lysosomes and mitochondria in living cells. J. Mater. Chem. B 3, 3315–3323 (2015)CrossRef
62.
N. Hayashi, T. Nishihara, T. Matsukihira, H. Nakashima, K. Miyabayashi, M. Miyake, H. Higuchi, Orientation and substituent effects on the properties of the diacetylene-group connected octaethylporphyrin–dihexylbithiophene derivatives (OEP–DHBTh–X) carrying electron-withdrawing groups. Bull. Chem. Soc. Jpn. 80, 371–386 (2007)CrossRef
63.
S. Roquet, A. Cravino, P. Leriche, O. Alévêque, P. Frère, J. Roncali, Triphenylamine–thienylenevinylene hybrid systems with internal charge transfer as donor materials for heterojunction solar cells. J. Am. Chem. Soc. 128, 3459–3466 (2006)CrossRef
Metadaten
Titel
Effects of donor position on dibenzofulvene-based organic dyes for photovoltaics
verfasst von
Giuseppina Anna Corrente
Eduardo Fabiano
Luisa De Marco
Gianluca Accorsi
Roberto Giannuzzi
Antonio Cardone
Giuseppe Gigli
Giuseppe Ciccarella
Agostina-Lina Capodilupo
Publikationsdatum
01.03.2017
Verlag
Springer US
Erschienen in
Journal of Materials Science: Materials in Electronics / Ausgabe 12/2017
Print ISSN: 0957-4522
Elektronische ISSN: 1573-482X
DOI
https://doi.org/10.1007/s10854-017-6594-2

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