The development and widespread application of organic electronic devices require the availability of simple and cost-effective suitable materials. In this study, the preparation of a new class of conjugated compounds on the basis of a dithienocyclohexanone (DTCH) core is reported. Several synthetic strategies for the preparation of dialkyl DTCH derivatives are explored, with special emphasis on the establishment of a sustainable synthetic access. Two successful synthetic pathways, both consisting of five steps, are identified: the first one featuring readily available 3-thiophenecarboxaldeyde and the second one 3-ethynylthiophene as the starting materials. Both procedures are characterized by reasonably high overall yields (over 30%) and remarkably low E factors (<400). Preliminary evidences of the use of such building blocks in the micellar Suzuki-Miyaura cross-coupling reactions leading to promising molecular semiconductors are also given. Moreover, on a small molecule containing DTCH moiety, solar cell performance was investigated.
Bianchi, G., Po, R., Sassi, M., Beverina, L., Chiaberge, S., Spera, S., et al. (2017). Synthesis of Dithienocyclohexanones (DTCHs) as a Family of Building Blocks for π-Conjugated Compounds in Organic Electronics. ACS OMEGA, 2(8), 4347-4355 [10.1021/acsomega.7b00987].
Synthesis of Dithienocyclohexanones (DTCHs) as a Family of Building Blocks for π-Conjugated Compounds in Organic Electronics
Sassi M.;Beverina L.;
2017
Abstract
The development and widespread application of organic electronic devices require the availability of simple and cost-effective suitable materials. In this study, the preparation of a new class of conjugated compounds on the basis of a dithienocyclohexanone (DTCH) core is reported. Several synthetic strategies for the preparation of dialkyl DTCH derivatives are explored, with special emphasis on the establishment of a sustainable synthetic access. Two successful synthetic pathways, both consisting of five steps, are identified: the first one featuring readily available 3-thiophenecarboxaldeyde and the second one 3-ethynylthiophene as the starting materials. Both procedures are characterized by reasonably high overall yields (over 30%) and remarkably low E factors (<400). Preliminary evidences of the use of such building blocks in the micellar Suzuki-Miyaura cross-coupling reactions leading to promising molecular semiconductors are also given. Moreover, on a small molecule containing DTCH moiety, solar cell performance was investigated.File | Dimensione | Formato | |
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