Abstract
A series of carbazole-thiophene dimers,P1–P9, were synthesized using Suzuki-Miyaura and Ullmann coupling reactions. InP1–P9, carbazole-thiophenes were linked at the N-9 position for different core groups via biphenyl, dimethylbiphenyl, and phenyl. Electronic properties were evaluated by UV-Vis, cyclic voltammogram, and theoretical calculations. Particularly, the effects of conjugation connectivity on photophysical and electrochemical properties, as well as the correlation between carbazole-thiophene and the core, were studied. Carbazole connecting with thiophenes at the 3,6-positions and the phenyl group as a core group leads to increased stabilization of HOMO and LUMO energy levels where the bandgap (ΔE) is significantly reduced.
Highlights
Organic photovoltaics (OPVs) are alternatives to amorphous silicon as materials for thin film solar cells
Various carbazole-thiophene hybrid oligomers that are used as functional materials by using their fluorescence and donor properties have been reported [21,22,23,24,25]; in particular, a large number of derivatives possessing the anchoring and acceptor groups used for organic solar cells (OSCs) have been recently synthesized since the pioneering work by Koumura, Hara, and coworkers [26,27,28,29,30,31,32]
The synthesis of compounds P1–P9 was described in three parts as outlined in Schemes 1 and 2
Summary
Organic photovoltaics (OPVs) are alternatives to amorphous silicon as materials for thin film solar cells. Π-Conjugated oligomers and polymers have attracted much attention in recent decades due to their potential uses as semiconductors and electroactive materials in various organic electronic devices such as organic field-effect transistors (OFETs), organic light emitting diodes (OLEDs), organic solar cells (OSCs), and nonlinear optical devices [2,3,4,5,6,7,8,9,10,11] These oligomers have an advantage in terms of convenient fine-tuning of electronic, photophysical, and electrochemical properties by rational structural modification to achieve optimal device performance. The synthesis, structural features, and electronic and photophysical properties of P4–P9 (Figure 1) according to UV-Vis, fluorescence spectroscopy, cyclic voltammetry, and theoretical calculations in comparison with reported compounds P1–P3 are described
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