Pyridalthiadiazole-Based Narrow Band Gap Chromophores
2012
π-Conjugated materials containing pyridal[2,1,3]thiadiazole (PT) units have recently achieved record power conversion efficiencies of 6.7% in solution-processed, molecular bulk-heterojunction (BHJ) organic photovoltaics. Recognizing the importance of this new class of molecular systems and with the aim of establishing a more concrete path forward to predict improvements in desirable solid-state properties, we set out to systematically alter the molecular framework and evaluate structure–property relationships. Thus, the synthesis and properties of 13 structurally related D1-PT-D2-PT-D1 compounds, where D represents a relatively electron-rich aromatic segment compared to PT, are provided. Physical properties were examined using a combination of absorption spectroscopy, cyclic voltammetry, thermal gravimetric analysis, differential scanning calorimetry, and solubility analysis. Changes to end-capping D1 units allowed for fine control over electronic energy levels both in solution and in the bulk. Substituti...
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