Abstract
Three novel indolo[3,2-b]carbazole-based dyes have been designed and synthesized using a 6,12-diphenyl substituted indolo[3,2-b]carbazole core as a π-conjugated donor, a thiophene cyanoacrylic acid moiety as electron acceptor and anchoring group, together with triphenylamine, 3,4,5-trimethoxybenzene and bromine as a second donor group. The photophysical and electrochemical properties of the dyes have been investigated by UV spectroscopy and cyclic voltammetry (CV). Our study indicates that the second donor plays the important role of improving dye aggregation as well as tuning the photoelectronic properties. These indolo[3,2-b]carbazole based dyes show good performances with high Voc of 0.75 V, FF of 0.72, and a moderate PCE of 3.11% under AM 1.5 irradiation.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
Notes and references
B. Liu and E. S., Aydil, Growth of oriented single-crystalline rutile TiO2 nanorods on transparent conducting substrates for dye-sensitized solar cells, J. Am. Chem. Soc., 2009, 131 3985–3990
A. Mishra, M. K. R. Fischer and P., Baeuerle, Metal-free organic dyes for dye-sensitized solar cells: from structure: property relationships to design rules, Angew. Chem., Int. Ed., 2009, 48 2474–2499
M. K. Nazeeruddin, F. De Angelis, S. Fantacci, A. Selloni, G. Viscardi, P. Liska, S. Ito, T. Bessho and M., Gratzel, Combined experimental and DFT-TDDFT computational study of photoelectrochemical cell ruthenium sensitizers, J. Am. Chem. Soc., 2005, 127 16835–16847
M., Gratzel, The advent of mesoscopic injection solar cells, Prog. Photovoltaics, 2006, 14 429–442
M. K. Nazeeruddin, S. M. Zakeeruddin, R. Humphry-Baker, M. Jirousek, P. Liska, N. Vlachopoulos, V. Shklover, C. H. Fischer and M., Gratzel, Acid−base equilibria of (2,2′-bipyridyl-4,4′-dicarboxylic acid)ruthenium(II) complexes and the effect of protonation on charge-transfer sensitization of nanocrystalline titania, Inorg. Chem., 1999, 38 6298–6305
X. Li, J. Gui, H. Yang, W. Wu, F. Li, H. Tian and C., Huang, A new carbazole-based phenanthrenyl ruthenium complex as sensitizer for a dye-sensitizd solar cells, Inorg. Chim. Acta, 2008, 361 2835–2840
C. Y. Chen, S. J. Wu, C. G. Wu, J. G. Chen and K. C., Ho, A ruthenium complex with super-high light-harvesting capacity for dye-sensitized solar cells, Angew. Chem., Int. Ed., 2006, 45 5822–5825
X. Lu, Q. Feng, T. Lan, G. Zhou and Z.-S. Wang, Molecular engineering of quinoxaline-based organic sensitizers for highly efficient and stable dye-sensitized solar sells, Chem. Mater., 2012, 24 3179–3187
D. H. Lee, M. J. Lee, H. M. Song, B. J. Song, K. D. Seo, M. Pastore, C. Anselmi, S. Fantacci, F. De Angelis, M. K. Nazeeruddin, M. Graeetzel and H. K., Kim, Organic dyes incorporating low-band-gap chromophores based on π-extended benzothiadiazole for dye-sensitized solar cells, Dyes Pigm., 2011, 91 192–198
J. He, W. Wu, J. Hua, Y. Jiang, S. Qu, J. Li, Y. Long and H., Tian, Bithiazole-bridged dyes for dye-sensitized solar cells with high open circuit voltage performance, J. Mater. Chem., 2011, 21 6054–6062
J. Song, F. Zhang, C. Li, W. Liu, B. Li, Y. Huang and Z., Bo, Phenylethyne-Bridged Dyes for Dye-Sensitized Solar Cells, J. Phys. Chem. C, 2009, 113 13391–13397
C.-Y. Chen, J.-G. Chen, S.-J. Wu, J.-Y. Li, C.-G. Wu and K.-C. Ho, Multifunctionalized ruthenium-based supersensitizers for highly efficient dye-sensitized solar cells, Angew. Chem., Int. Ed., 2008, 47 7342–7345
C. S. Karthikeyan, H. Wietasch and M., Thelakkat, Highly efficient solid-state dye-sensitized TiO2 solar cells using donor-antenna dyes capable of multistep charge-transfer cascades, Adv. Mater., 2007, 19 1091–1095
Q. Chai, W. Li, J. Liu, Z. Geng, H. Tian and W.-H. Zhu, Rational molecular engineering of cyclopentadithiophene-bridged D-A-π-A sensitizers combining high photovoltaic efficiency with rapid dye adsorption, Sci. Rep., 2015, 5 11330
Z. Ning, Q. Zhang, W. Wu, H. Pei, B. Liu and H., Tian, Starburst triarylamine based dyes for efficient dye-sensitized solar cells, J. Org. Chem., 2008, 73 3791–3797
T. Kaewpuang, N. Prachumrak, S. Namuangruk, S. Jungsuttiwong, T. Sudyoadsuk, P. Pattanasattayavong and V., Promarak, (D-π-)2D-π-A-Type organic dyes for efficient dye-sensitized solar cells, Eur. J. Org. Chem., 2016, 2528–2538
S. Fuse, R. Takahashi, M. M. Maitani, Y. Wada, T. Kaiho, H. Tanaka and T., Takahashi, Synthesis and evaluation of thiophene-based organic dyes containing a rigid and nonplanar donor with secondary electron donors for use in dye-sensitized solar cells, Eur. J. Org. Chem., 2016, 508–517
S. Namuangruk, R. Fukuda, M. Ehara, J. Meeprasert, T. Khanasa, S. Morada, T. Kaewin, S. Jungsuttiwong, T. Sudyoadsuk and V., Promarak, D-D−π-A-Type organic dyes for dye-sensitized solar cells with a potential for direct electron injection and a high extinction coefficient: synthesis, characterization, and theoretical investigation, J. Phys. Chem. C, 2012, 116 25653–25663
M.-D. Zhang, H.-X. Xie, X.-H. Ju, L. Qin, Q.-X. Yang, H.-G. Zheng and X.-F. Zhou, D-D-π-A organic dyes containing 4,4′-di(2-thienyl)triphenylamine moiety for efficient dye-sensitized solar cells, Phys. Chem. Chem. Phys., 2013, 15 634–641
G. Wu, F. Kong, J. Li, X. Fang, Y. Li, S. Dai, Q. Chen and X., Zhang, Triphenylamine-based organic dyes with julolidine as the secondary electron donor for dye-sensitized solar cells, J. Power Sources, 2013, 243 131–137
T. Sudyoadsuk, S. Pansay, S. Morada, R. Rattanawan, S. Namuangruk, T. Kaewin, S. Jungsuttiwong and V., Promarak, Synthesis and characterization of D-D-π-A-Type organic dyes bearing carbazole-carbazole as a donor moiety (D-D) for efficient dye-sensitized solar cells, Eur. J. Org. Chem., 2013, 5051–5063
Z. Ning and H., Tian, Triarylamine: a promising core unit for efficient photovoltaic materials, Chem. Commun., 2009, 5483–5495
L.-L. Tan, J.-F. Huang, Y. Shen, L.-M. Xiao, J.-M. Liu, D.-B. Kuang and C.-Y. Su, Highly efficient and stable organic sensitizers with duplex starburst triphenylamine and carbazole donors for liquid and quasi-solid-state dye-sensitized solar cells, J. Mater. Chem. A, 2014, 2 8988–8994
C. Teng, X. Yang, C. Yuan, C. Li, R. Chen, H. Tian, S. Li, A. Hagfeldt and L., Sun, Two novel carbazole dyes for dye-sensitized solar cells with open-circuit voltages up to 1 V based on Br-/Br3− electrolytes, Org. Lett., 2009, 11 5542–5545
G. Marotta, M. A. Reddy, S. P. Singh, A. Islam, L. Han, F. De Angelis, M. Pastore and M., Chandrasekharam, Novel carbazole-phenothiazine dyads for dye-sensitized solar cells: a combined experimental and theoretical study, ACS Appl. Mater. Interfaces, 2013, 5 9635–9647
S. Cai, X. Hu, Z. Zhang, J. Su, X. Li, A. Islam, L. Han and H., Tian, Rigid triarylamine-based efficient DSSC sensitizers with high molar extinction coefficients, J. Mater. Chem. A, 2013, 1 4763–4772
Y. Liang, B. Peng and J. Chen, Correlating dye adsorption behavior with the open-circuit voltage of triphenylamine-based dye-sensitized solar cells, J. Phys. Chem. C, 2010, 114 10992–10998
S. Chen, J. Wei, K. Wang, C. Wang, D. Chen, Y. Liu and Y., Wang, Constructing high-performance blue, yellow and red electroluminescent devices based on a class of multifunctional organic materials, J. Mater. Chem. C, 2013, 1 6594–6602
H.-C. Ting, Y.-M. Chen, H.-W. You, W.-Y. Hung, S.-H. Lin, A. Chaskar, S.-H. Chou, Y. Chi, R.-H. Liu and K.-T. Wong, Indolo[3,2-b]carbazole/benzimidazole hybrid bipolar host materials for highly efficient red, yellow, and green phosphorescent organic light emitting diodes, J. Mater. Chem., 2012, 22, 8399–8407
X. H. Zhang, Z. S. Wang, Y. Cui, N. Koumura, A. Furube and K. Hara, Organic Sensitizers Based on Hexylthiophene-Functionalized Indolo[3,2-b]carbazole for efficient Dye-Sensitized Solar Cells, J. Phys. Chem. C, 2009, 113, 13409–13415
H. Choi, C. Baik, S. O. Kang, J. Ko, M.-S. Kang, M. K. Nazeeruddin and M. Gratzel, Highly efficient and thermally stable organic sensitizers for solvent-free dye-sensitized solar cells, Angew. Chem., Int. Ed., 2008, 47 327–330
S. M. Zakeeruddin, M. K. Nazeeruddin, R. Humphry-Baker, P. Pechy, P. Quagliotto, C. Barolo, G. Viscardi and M. Gratzel, Design, synthesis, and application of amphiphilic ruthenium polypyridyl photosensitizers in solar cells based on nanocrystalline TiO2 films, Langmuir, 2002, 18 952–954
T. Horiuchi, H. Miura, K. Sumioka and S. Uchida, High efficiency of dye-sensitized solar cells based on metal-free indoline dyes, J. Am. Chem. Soc., 2004, 126 12218–12219
T. Daeneke, T.-H. Kwon, A. B. Holmes, N. W. Duffy, U. Bach and L. Spiccia, High-efficiency dye-sensitized solar cells with ferrocene-based electrolytes, Nat. Chem., 2011, 3 211–215
T. Higashino, Y. Fujimori, K. Sugiura, Y. Tsuji, S. Ito and H. Imahori, Tropolone as a high-performance robust anchoring group for dye-sensitized solar cells, Angew. Chem. Int. Ed., 2015, 54 9052–9056
K. Kurotobi, Y. Toude, K. Kawamoto, Y. Fujimori, S. Ito, P. Chabera, V. Sundström and H. Imahori, Highly asymmetrical porphyrins with enhanced push-pull character for dye-sensitized solar cells, Chem. - Eur. J., 2013, 19 17075–17081
J. Nissfolk, K. Fredin, A. Hagfeldt and G. Boschloo, Recombination and transport processes in dye-sensitized solar cells investigated under working conditions, J. Phys. Chem. B, 2006, 110 17715–17718
Q. Wang, Z. Zhang, S. M. Zakeeruddin and M. Grätzel, Enhancement of the performance of dye-sensitized solar cell by formation of shallow transport levels under visible light Illumination, J. Phys. Chem. C, 2008, 112 7084–7092
Y. Wu and W. Zhu, Organic sensitizers from D-π-A to D-A-π-A: effect of the internal electron-withdrawing units on molecular absorption, energy Levels and photovoltaic performances, Chem. Soc. Rev., 2013, 42 2039–2058
Y. Wu, M. Marszalek, S. M. Zakeeruddin, Q. Zhang, H. Tian, M. Gratzel and W., Zhu, High-conversion-efficiency organic dye-sensitized solar cells: molecular engineering on D-A-π-A featured organic indoline dyes, Energy Environ. Sci., 2012, 5 8261–8272
S. W. Park, K.-I. Son, M. J. Ko, K. Kim and N.-G. Park, Effect of donor moiety in organic sensitizer on spectral response, electrochemical and photovoltaic properties, Synth. Met., 2009, 159 2571–2577
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Xiao, Z., Di, Y., Tan, Z. et al. Efficient organic dyes based on perpendicular 6,12-diphenyl substituted indolo[3,2-b]carbazole donor. Photochem Photobiol Sci 15, 1514–1523 (2016). https://doi.org/10.1039/c6pp00286b
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/c6pp00286b