Boya Duyarlı Güneş Pillleri için Karbazol Tiyofen Türevli Moleküllerin Sentezi ve Karakterizasyonu

Year 2021, Volume: 16 Issue: 1, 179 - 188, 27.05.2021

Çiğdem Erden , Kamuran Görgün

https://doi.org/10.29233/sdufeffd.751760

Abstract

Bu çalışmada ilk olarak, karbazol başlangıç maddesi kullanılarak, N-bromo süksinimid ile bromlama reaksiyonu yapılmış ve 3,6-dibromokarbazol (II) elde edilmiştir. Daha sonra, 3,6-dibromokarbazol (II) ve oktil bromür kullanılarak alkilleme reaksiyonu yapılmış ve 3,6-dibromo-9-oktilkarbazol (III) elde edilmiştir. Son aşamada ise Suzuki-Miyaura çapraz kenetlenme reaksiyonu ile farklı arilboronik asitler kullanılarak, D-A sistemine uygun literatürde olmayan yeni karbazol türevli maddeler 3,6-bis-benzo[b]tiyofen-2-il-9-oktil-9H-karbazol (IV) ve 3,6-bis-(5-kloro-tiyofen-2-il)-9-oktilkarbazol (V) sentezlenmiştir. Sentezlenen bu maddelerin yapıları 1H-NMR ve 13C-NMR spektroskopik yöntemler kullanılarak aydınlatılmıştır. Ayrıca yeni sentezlenen IV ve V numaralı moleküllerin, boya duyarlı güneş pillerinde (BDGP) boya malzemesi olarak kullanımı da araştırılmıştır. Bunun için BDGP-IV ve BDGP-V kodlu piller hazırlanıp, elektriksel karakterizasyonları yapılmıştır.

Keywords

Karbazol, Suzuki-Miyaura, Boya Duyarlı Güneş Pilleri

Thanks

Boya Duyarlı Güneş Pillerinin fabrikasyonu ve ölçümlerindeki katkılardan dolayı Eskişehir Teknik Üniversitesi Fen Fakültesi öğretim üyesi Prof. Dr. Yasemin Çağlar’a teşekkür ederiz.

Synthesis and Characterization of Carbazole Thiophene Derived Molecules for Dye Sensitized Solar Cells

Abstract

In this study, firstly, the bromination reaction with N-bromo succinimide was carried out using the carbazole as a starting material and 3,6-dibromocarbazole (II) was obtained. Then, the alkylation reaction was carried out which was using octyl bromide with 3,6-dibromocarbazole to obtain 3,6-dibromo-9-octylcarbazole (III). In the last stage, the novel carbazole-derived substances 3,6-bis-benzo[b]tiyofen-2-il-9-oktil-9H-karbazol (IV) and 3,6-bis-(5-kloro-tiyofen-2-il)-9-oktilkarbazol (V) which is suitable for the D-A system and do not exist in the literature were synthesized with Suzuki-Miyaura cross-coupling reaction by using different arylboronic acids. Characterizations of these synthesized substances were performed by using 1H-NMR and 13C-NMR spectroscopic methods. In addition, it has been investigated the usage as dye materials of these synthesized substances in dye sensitized solar cells (BDGP). In this scope, BDGP-IV and BDGP-V cells were fabricated and their electrical characterizations were performed.

Keywords

Carbazole, Suzuki-Miyaura, Dye sensitized solar cells.

References

• [1] Z. Bouaziz, S. Issa, J. Gentili, A. Gratz, A. Bollacke, and M. Kassack, “Biologically active carbazole derivatives: focus on oxazinocarbazoles and related compounds,” J. Enzyme Inhib., 30, 180-188, 2014.
• [2] T. H. Behrens, “Microchemical distinction of the hydrocarbons of coal tar,” Recl Trav. Chim Pays-Bas, 19, 386-397, 1900.
• [3] E. Drechsel , “Borsche-Drechsel cyclization,” J. Prakt. Chem, 38 (2), 69-72, 1858.
• [4] A. S. Sarac, E. Sezer, and B. Ustamehmetoglu, “Oxidative polymerization of N-substituted carbazoles,” Polym. Adv. Technol., 8 (9), 556-562, 1997.
• [5] G. Mengoli, M. M. Musiani, B. Schreck, and S. Zecchin, “Electrochemical synthesis and properties of polycarbazole films in protic acid media‖,” J. Electroanal. Chem. Interf. Electrochem., 246 (1), 73-86, 1988.
• [6] S. Özgün, “Bazı Karbazol Bileşiklerinin TCNE ve TNM ile Yük Transfer Kompleksleşmeleri,” Yüksek Lisans Tezi, Kimya Bölümü, Balıkesir Üniv., Balıkesir, Türkiye, 2016.
• [7] M. Çağlı, “Sübstitüe Karbazollerin Sentezi, Karakterizasyonu ve Hesapsal Çalışmaları,” Yüksek Lisans Tezi, Kimya Bölümü, Balıkesir Üniv., Balıkesir, Türkiye, 2014.
• [8] S. Ameen, S. B. Lee, S. C. Yoon, J. Lee and C. Lee, “Diphenylaminocarbazoles by 1,8-functionalization of carbazole: Materials and application to phosphorescent organic light-emitting diodes,” Dyes Pigm., 124, 35-44, 2016.
• [9] N. Berton, R. Nakar, and B. Schmaltz, “DMPA-containing carbazole-based hole transporting materials for perovskite solar cells: Recent advances and perspectives,” Synth. Met., 252, 91-106, 2019.
• [10] G. Sathiyan, E.K.T. Sivakumar, R. Ganesamoorthy, R. Thangamuthuc and P. Sakthivela, “Review of carbazole based conjugated molecules for highly efficient organic solar cell application,” Tetrahedron Lett., 57, 243–252, 2016
• [11] T.N. Murakami, N. Koumura, “Development of next-generation organic-based solar cells: Studies on de-sensitized and perovskite solar cells,” Adv. Energy Mater., 9, 1802967, 2019.
• [12] J. Massin, L. Ducasse, M. Abbas, L. Hirsch, T. Toupance, C. Olivier, “Molecularengineering of carbazole–fluorene sensitizers for high open-circuit voltage DSSCs: synthesis and performance comparison with iodine and cobalt electrolytes,” Dyes Pigments, 118, 76–87, 2015.
• [13] K.S.V. Gupta, J. Zhang, G. Marotta, M.A. Reddy, S.P. Singh, A. Islam, L. Han, F. De Angelis, M. Chandrasekhram, M. Pastore, “Effect of the anchoring group in the performance of carbazole–phenothiazine dyads for dye-sensitized solar cells,” Dyes Pigments, 113, 536–545, 2015.
• [14] F. Dinçer, “Türkiye’de Güneş Enerjisinden Elektrik Üretimi Potansiyeli – Ekonomik Analizi ve AB Ülkeleri ile Karşılaştırmalı Değerlendirme,” KSU J. Eng. Sci, 14, 8-17, 2011.
• [15] D.K. Kumar, J. Krˇızˇ, N. Bennett, B. Chen, H. Upadhayaya, K.R. Reddy, and V. Sadhu, “Functionalized metal oxide nanoparticles for efficient dye-sensitized solar cells (DSSCs): A review,” Mater. Sci. Energ. Tech., 3, 472–481, 2020.
• [16] B. O’regan and M. Gratzel, “A low-cost high- efficiency solar cell based on dye-sensitized colloidal TiO2 films,” Nature, 353, 737-740, 1991.
• [17] I. N. Obotowo, I.B. Obot, and U.J. Ekpe, “Organic sensitizers for dye-sensitized solar cell (DSSC): Properties from computation, progress and future perspective,” J. Mol. Struct., 1122, 80-87, 2016.
• [18] Y. Li, J. Ding, M. Day, Y. Tao, J. Lu, and M. D’iorio, “Synthesis and Properties of Random and Alternating Fluorene/Carbazole Copolymers for Use in Blue Light-Emitting Devices,” Chem. Mater., 16, 2165-2173, 2004.
• [19] Ç. Erden, “Karbazol türevli maddelerin sentezlenmesi, karakterizasyonu ve güneş pili uygulamaları,” Yüksek Lisans Tezi, Kimya Bölümü, Eskişehir Osmangazi Üniv., Eskişehir, Türkiye, 2018.
• [20] P. Pansay, N. Prachumrak, S. Jungsuttiwong, T. Keawin, T. Taweesak Sudyoadsuk, and V. Promarak “Multibromo-N-alkylcarbazoles: synthesis, characterization, and their benzo[b]thiophene derivatives,” Tetrahedron Lett., 53, 4568–4572, 2012.