Electronegative oligothiophenes fully annelated with hexafluorocyclopentene: synthesis, properties, and intrinsic electron mobility.

Synthesis of hexafluorocyclopenta[c]thiophene-repeated oligothiophenes up to 6-mer has been accomplished. The photophysical and electrochemical properties of these oligomers unambiguously exemplify marked electronegative character without disrupting the effective conjugation. The combination of time-resolved microwave conductivity and transient optical spectroscopy measurements of the 6-mer revealed the intrinsic electron mobility to be as high as 2.0 x 10(-1) cm(2) V(-1) s(-1).

Electronegative oligothiophenes based on difluorodioxocyclopentene-annelated thiophenes: synthesis, properties, and n-type FET performances.

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).

Electronegative oligothiophenes based on a hexafluorocyclopentene-annelated thiophene unit.

[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.

Two-dimensional networks of ethylenedithiotetrathiafulvalene derivatives with the hydrogen-bonded functionality of uracil, and channel structure of its tetracyanoquinodimethane complex.

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.