A series of oligothiophenes containing difluorodioxocyclopentene-annelated thiophene units was synthesized, and their electronic properties and structures were investigated by spectroscopic and electrochemical measurements and X-ray analyses. The oligothiophenes having the terminal difluorodioxocyclopentene annelations showed n-type semiconducting behavior on FET devices, and the quaterthiophene revealed field-effect electron mobility as high as 1.3 x 10(-2) cm2 V(-1) s(-1).
The syntheses of perfluoroalkyl-annelated conjugated units: hexafluorocyclopenta[c]thiophene, 4,4-difluoro-4H-cyclopenta[2,1-b:3,4-b']dithiophene, and 6,6,12,12-tetrafluoroindeno[3,2-b]fluorine, and these-containing oligomers have been accomplished. The annelation of the perfluoroalkyl groups effectively lowers the lowest unoccupied molecular orbitral (LUMO) energy levels without disrupting the effective conjugation of the backbones, which was unambiguously clarified by spectroscopic and electrochemical measurements as well as X-ray analysis. The perfluoroalkyl-annelated oligothiophenes exhibited n-type semiconducting behavior with field-effect electron mobility up to 0.018 cm2 V-1 s-1.
[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.
Ethylenedithiotetrathiafulvalene (EDT-TTF) derivatives with N1-butyluracil or N1-phenyluracil moiety were designed and synthesized as new hydrogen-bonded electron-donor molecules with the aim of introducing multiple S...S interactions into the hydrogen-bonded structures composed of the TTF-nucleobase systems. In the crystals of the EDT-TTF derivatives, two-dimensional sheet and layer structures were formed through pi...pi, multiple S...S interactions, and complementary double hydrogen bonds. In the tetracyanoquinodimethane (TCNQ) charge-transfer complex of the EDT-TTF-N1-butyluracil dyad with a segregated column, a layer structure of the electron-donor molecules was constructed through the noncovalent interactions. The n-butyl group of the uracil moiety served to separate the space between the donor layers, resulting in construction of a channel structure. Disordered TCNQ molecules were located in the microporous space of the channel. The TCNQ complex exhibited high electric conductivity (sigmart= 2.1 S cm(-1)) in a single crystal.
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