Studies in Thiophene Chemistry for Organic Electronic Materials

Thiophene-based organic semiconductor materials have seen important growth in the last two decades owing to their potential applications in many different areas. Overall, this thesis details attempts to develop rapid, efficient, cheap and scalable syntheses of small molecules and monomers of thiophene-based molecules. After an introductory Chapter, the second Chapter in this thesis focuses on the synthesis of 7-R-anthra[2,3-b]thiophenes derivatives 11a-d (R = H, Me, iPr, OMe) and naphtho[2,3-b:6,7-b']dithiophene 12. Existing synthetic methods for the known anthra[2,3-b]thiophene 11a and naphtho[2,3-b:6,7-b']dithiophene 12 require multi-steps, toxic reagents, expensive starting materials and give low yields. However, we prepared these 7-R-anthra[2,3-b]thiophene derivatives 11a-d (R = H, Me, iPr, MeO) in only three steps (with average overall yields of >50%) starting from (E)-4-RC6H4CH2(HOCH2)C=CI(CH2OH). The latter are commercial or readily prepared from 2-butyne-1,4-diol 1 and ArCH2Cl 4 (both typically costing