Electronegative Oligothiophenes Based on a Hexafluorocyclopentene-Annelated Thiophene Unit

Abstract

[Structure: see text] The synthesis of hexafluorocyclopenta[c]thiophene and its based oligothiophenes is described. The effectiveness of a hexafluorocyclopentene unit to lower the LUMO level without disturbing the effective conjugation could be unambiguously clarified by spectroscopic measurements and X-ray analysis.

Synthesis and Structural Study of 4H‐Cyclopenta[c]thiophene‐5,5(6H)‐dicarbonitrile and 6,6‐Dimethyl‐1,4‐dihydro‐5H‐cyclopenta[d][1,2]dithiine‐5,7(6H)‐dione

“…Synthesis of CPT was reported from Mac Dowell et al in 1966 . Pioneer work regarding the synthesis of different CPT and their application in OFETs has been reported later by Y. Aso et al . and Zade et al .…”

Development of donor–acceptor copolymers based on dioxocycloalkene-annelated thiophenes as acceptor units for organic photovoltaic materials

“…We previously reported that the hexafluorocyclopenta[c]thiophene (F) 14 repeated oligothiophenes (F 2 , F 4 and F 6 ) ( Figure 1a) clearly showed a positive shift of the electrochemical reduction potential and red shift of the absorption maximum as the number of the F units increased. 15 These results clearly indicate that the annelation of hexafluorocyclopentene at the thiophene rings contributes to an increase in the electron-accepting nature of π-conjugated systems without disrupting the effective conjugation.…”

Air‐Stable n‐Type Organic Field‐Effect Transistors Based on Carbonyl‐Bridged Bithiazole Derivatives

“…Significant progress has recently been made in the development of p‐type OFET materials 2. However, limited studies have been conducted on the development of n‐type OFET materials 3–14. This is because of the insufficiency of their molecular design in stabilizing electron‐injected species and arranging the molecular ordering for efficient electron transport in the solid state.…”