T-grafting BODIPY-Based Photosensitizers: The Synthesis of 2,6-Diethylacrylic-8-( o -methoxyphenyl)BODIPY and Its DSSC Performance

Reinner Ishaq Lerrick; Wastiana Bere; Meliana Da Silva Braga; Agus Supriyanto; Ali Hashem Essa

doi:10.22146/ijc.76919

T-grafting BODIPY-Based Photosensitizers: The Synthesis of 2,6-Diethylacrylic-8-(o-methoxyphenyl)BODIPY and Its DSSC Performance

https://doi.org/10.22146/ijc.76919

Reinner Ishaq Lerrick^(1*), Wastiana Bere⁽²⁾, Meliana Da Silva Braga⁽³⁾, Agus Supriyanto⁽⁴⁾, Ali Hashem Essa⁽⁵⁾

(1) Department of Chemistry, Faculty of Science and Engineering, University of Nusa Cendana, Jl. Adi Sucipto, Penfui-Kupang 85118, NTT, Indonesia
(2) Department of Chemistry, Faculty of Science and Engineering, University of Nusa Cendana, Jl. Adi Sucipto, Penfui-Kupang 85118, NTT, Indonesia
(3) Department of Chemistry, Faculty of Science and Engineering, University of Nusa Cendana, Jl. Adi Sucipto, Penfui-Kupang 85118, NTT, Indonesia
(4) Department of Physics, Faculty of Mathematics and Natural Sciences, Universitas Sebelas Maret, Jl. Ir. Sutami 36A, Kentingan, Surakarta 57126, Indonesia
(5) Department of Chemistry, College of Science, University of Basrah, Basrah 61004, Iraq
(*) Corresponding Author

Abstract

A new T-grafting photosensitizer of Dye-Sensitized Solar Cell (DSSC) has been developed by aligning Donor-Acceptor (D-A) group in an axially chiral BODIPY. Synthesis of the dye was conducted over a linear approach involving one-pot, non-oxidative synthesis of 1,3,5,7-tetramethyl-8-(o-methoxyphenyl)BODIPY, bromination, and finally C2/C6 ethyl acrylate Pd-Heck coupling to produce 65% of 2-ethylacrylic-1,3,5,7-tetramethyl-8-(o-methoxyphenyl)BODIPY (BOD-8) and 35% of 2,6-diethylacrylic-1,3,5,7-tetramethyl-8-(o-methoxyphenyl)BODIPY (BOD-9), both characterized by the appearance of acrylic alkenes at 6.05, and 7.63 ppm for BOD-8, and the additional 5.43, 7.80 ppm doublet peaks for BOD-9. The resulting dye showed excellent photon harvesting-related photovoltaic properties and electronic injection and regeneration processes where the acrylic esters were found to be the Donor and the aryl was the Acceptor. Eventually, the dye produced a current at 0.5% efficiency, similar to the horizontal D-A DSSC photosensitizer design.

Keywords

DSSC photosensitizer; T-grafted alignment; axially chiral BODIPY

Full Text:

Full Text PDF Full Text PDF-Suppl. Data

References

[1] Squeo, B.M., Ganzer, L., Virgili, T., and Pasini, M., 2020, BODIPY-based molecules, a platform for photonic and solar cells, Molecules, 26 (1), 153.

[2] Saravanan, V., Ganesan, S., and Rajakumar, P., 2020, Synthesis and DSSC application of BODIPY decorated triazole bridged and benzene nucleus cored conjugated dendrimers, RSC Adv., 10 (31), 18390–18399.

[3] Awuah, S.G., and You, Y., 2012, Boron dipyrromethene (BODIPY)-based photosensitizers for photodynamic therapy, RSC Adv., 2 (30), 11169–11183.

[4] Merkes, J.M., Lammers, T., Kancherla, R., Rueping, M., Kiessling, F., and Banala, S., 2020, Tuning optical properties of BODIPY dyes by pyrrole conjugation for photoacoustic imaging, Adv. Opt. Mater., 8 (11), 1902115.

[5] Lerrick, R.I., Winstanley, T.P.L., Haggerty, K., Wills, C., Clegg, W., Harrington, R.W., Bultinck, P., Herrebout, W., Benniston, A.C., and Hall, M.J., 2014, Axially chiral BODIPYs, Chem. Commun., 50 (36), 4714–4716.

[6] Radunz, S., Kraus, W., Bischoff, F.A., Emmerling, F., Tschiche, H.R., and Resch-Genger, U., 2020, Temperature- and structure-dependent optical properties and photophysics of BODIPY dyes, J. Phys. Chem. A, 124 (9), 1787–1797.

[7] Feng, Z., Jiao, L., Feng, Y., Yu, C., Chen, N., Wei, Y., Mu, X., and Hao, E., 2016, Regioselective and stepwise syntheses of functionalized BODIPY dyes through palladium-catalyzed cross-coupling reactions and direct C-H arylations, J. Org. Chem., 81 (15), 6281–6291.

[8] Klfout, H., Stewart, A., Elkhalifa, M., and He, H., 2017, BODIPYs for dye-sensitized solar cells, ACS Appl. Mater. Interfaces, 9 (46), 39873–39889.

[9] Shah, M.F., Mirloup, A., Chowdhury, T.H., Sutter, A., Hanbazazah, A.S., Ahmed, A., Lee, J.J., Abdel-Shakour, M., Leclerc, N., Kaneko, R., and Islam, A., 2020, Cross-conjugated BODIPY pigment for highly efficient dye sensitized solar cells, Sustainable Energy Fuels, 4 (4), 1908–1914.

[10] Mao, M., and Song, Q.H., 2016, The structure-property relationships of D-π-A BODIPY dyes for dye-sensitized solar cells, Chem. Rec., 16 (2), 719–733.

[11] Lu, H., Mack, J., Yang, Y., and Shen, Z., 2014, Structural modification strategies for the rational design of red/NIR region BODIPYs, Chem. Soc. Rev., 43 (13), 4778–4823.

[12] Hosseinnezhad, M., Gharanjig, K., and Moradian, S., 2020, New D–A–π–A organic photo-sensitizer with thioindoxyl group for efficient dye-sensitized solar cells, Chem. Pap., 74 (5), 1487–1494.

[13] Liu, M., Ma, S., She, M., Chen, J., Wang, Z., Liu, P., Zhang, S., and Li, J., 2019, Structural modification of BODIPY: Improve its applicability, Chin. Chem. Lett., 30 (10), 1815–1824.

[14] Sunahara, H., Urano, Y., Kojima, H., and Nagano, T., 2007, Design and synthesis of a library of BODIPY-based environmental polarity sensors utilizing photoinduced electron-transfer-controlled fluorescence ON/OFF switching, J. Am. Chem. Soc., 129 (17), 5597–5604.

[15] Ren, W., Xiang, H., Peng, C., Musha, Z., Chen, J., Li, X., Huang, R., and Hu, Y., 2018, Direct C-H functionalization of difluoroboron dipyrromethenes (BODIPYs) at β-position by iodonium salts, RSC Adv., 8 (10), 5542–5549.

[16] Chen, J., Mizumura, M., Shinokubo, H., and Osuka, A., 2009, Functionalization of boron dipyrrin (BODIPY) dyes through iridium and rhodium catalysis: A complementary approach to α-and β-substituted BODIPYs, Chem. - Eur. J., 15 (24), 5942–5949.

[17] Farfán-Paredes, M., González-Antonio, O., Tahuilan-Anguiano, D.E., Peón, J., Ariza, A., Lacroix, P.G., Santillan, R., and Farfán, N., 2020, Physicochemical and computational insight of ¹⁹F NMR and emission properties of meso-(o-aryl)-BODIPYs, New J. Chem., 44 (45), 19459–19471.

[18] Hattori, S., Ohkubo, K., Urano, Y., Sunahara, H., Nagano, T., Wada, Y., Tkachenko, N.V., Lemmetyinen, H., and Fukuzumi, S., 2005, Charge separation in a nonfluorescent donor-acceptor dyad derived from boron dipyrromethene dye, leading to photocurrent generation, J. Phys. Chem. B, 109 (32), 15368–15375.

[19] Cui, Y., Yao, H., Zhang, J., Zhang, T., Wang, Y., Hong, L., Xian, K., Xu, B., Zhang, S., Peng, J., Wei, Z., Gao, F., and Hou, J., 2019, Over 16% efficiency organic photovoltaic cells enabled by a chlorinated acceptor with increased open-circuit voltages, Nat. Commun., 10 (1), 2515.

[20] Bessette, A., and Hanan, G.S., 2014, Design, synthesis and photophysical studies of dipyrromethene-based materials: Insights into their applications in organic photovoltaic devices, Chem. Soc. Rev., 43 (10), 3342–3405.

DOI: https://doi.org/10.22146/ijc.76919