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Molecules 2017, 22(10), 1607; doi:10.3390/molecules22101607

Small Molecules Derived from Thieno[3,4-c]pyrrole-4,6-dione (TPD) and Their Use in Solution Processed Organic Solar Cells

1
Research Group of Optical Properties of Materials (GPOM), Centro de Investigaciones en Óptica, A.P. 1-948, 37000 León, Guanajuato, Mexico
2
Instituto de Investigaciones Químico Biológicas Universidad Michoacana de San Nicolás de Hidalgo Edificio B-1. Ciudad Universitaria, 58030 Morelia, Michoacán, Mexico
3
Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Avenida Instituto Politécnico Nacional 2508 Colonia San Pedro Zacatenco, 07360 Mexico, D.F., Mexico
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Autónoma de Coahuila, Ing. José Cárdenas Valdez, República, 25280 Saltillo, Coahuila, México. Current address
Centro de Investigación en Química Aplicada, Boulevard E. Reyna 140, 25100 Saltillo, Mexico. Current address
§
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Del. Coyoacán, 04510 Ciudad de Mexico, Mexico. Current address
*
Authors to whom correspondence should be addressed.
Received: 18 August 2017 / Revised: 14 September 2017 / Accepted: 22 September 2017 / Published: 30 September 2017
(This article belongs to the Special Issue Direct (Hetero)Arylation: A New Tool for Organic Electronics)
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Abstract

In this work, microwave synthesis, chemical, optical and electrochemical characterization of three small organic molecules, TPA-TPD, TPA-PT-TPD and TPA-TT-TPD with donor-acceptor structure and their use in organic photovoltaic cells are reported. For the synthesis, 5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione was used as electron withdrawing fragment while the triphenylamine was used as electron donating fragment. Molecular electronic geometry and electronic distribution density were established by density functional theory (DFT) calculations and confirmed by optical and chemical characterization. These molecules were employed as electron-donors in the active layer for manufacturing bulk heterojunction organic solar cells, where [6,6]-phenyl C71 butyric acid methyl ester (PC71BM) was used as electron-acceptor. As cathode, Field′s metal (FM), an eutectic alloy (Bi/In/Sn: 32.5%, 51%, and 16.5%, respectively) with a melting point above 62 °C, was easily deposited by drop casting under vacuum-free process and at air atmosphere. Prepared devices based on TPA-TPD:PC71BM (1:4 w/w ratio) presented a large VOC = 0.97 V, with JSC = 7.9 mA/cm2, a FF = 0.34, then, a power conversion efficiency (PCE) of 2.6%. View Full-Text
Keywords: organic small molecules; microwave synthesis; donor-acceptor-donor structure; organic solar cells organic small molecules; microwave synthesis; donor-acceptor-donor structure; organic solar cells
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Garcias-Morales, C.; Romero-Borja, D.; Maldonado, J.-L.; Roa, A.E.; Rodríguez, M.; García-Merinos, J.P.; Ariza-Castolo, A. Small Molecules Derived from Thieno[3,4-c]pyrrole-4,6-dione (TPD) and Their Use in Solution Processed Organic Solar Cells. Molecules 2017, 22, 1607.

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