Synthesis and Structure of Alkyl-Substituted Fused Thiophenes Containing up to Seven Rings

• Published in: Journal of organic chemistry Vol. 72; no. 2; pp. 442 - 451
• Main Authors: He, Mingqian, Zhang, Feixia
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 19.01.2007; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; AROMATIC-HYDROCARBONS; POLYMERS; TRANSISTORS; SEMICONDUCTOR; CRYSTAL; HIGH-MOBILITY; THIN-FILM; DERIVATIVES; Organic solvent; Thiophene derivatives; Sulfur heterocycle; Electronic properties; Stability; Molecular structure; Pi-System; Solubility; Chemical synthesis; X ray diffraction; Crystalline structure
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo061853y

We have established a series of synthetic methods to synthesize alkyl-substituted fused thiophenes with degrees of fusion from two to seven rings. These fused thiophene ring compounds have very good solubility in common organic solvents, making possible the solution processing of these compounds for electronic applications. The UV absorption of these fused thiophenes is blue-shifted when compared with their hydrocarbon counterparts. The larger band gaps result in much better stability. Single-crystal X-ray results for 3,6-didecanyldithieno[2,3-d:2‘,3‘-d‘]thieno[3,2-b:4,5-b‘ ‘]dithiophene (FT5) and 3,7-didecanylthieno[3,2-b]thieno[2‘,3‘:4,5]thieno[2,3-d]thiophene (FT4) demonstrate that both compounds form π-stacking structures instead of a herringbone-type of packing motif. This more favorable π-stacked structure may lead to better material electronic properties such as mobility in devices fabricated with these compounds.