Fluorinated Thiophenes and Their Analogues

Serdyuk, Olga V.; Абаев, Владимир Т.; Бутин, А. В.; Nenajdenko, Valentine G.

doi:10.1007/978-3-319-04346-3_6

Cited by 2 publications

(1 citation statement)

References 182 publications

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“…There have been relatively few examples of either oligomeric or polymeric materials containing fluorinated thiophene. This paucity is probably related to the synthetic complexity of obtaining fluorinated thiophene building blocks . Perfluorinated thiophene oligomers from the trimer to the hexamer have been reported by Suzuki and co-workers .…”

Section: Introductionmentioning

confidence: 99%

Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes

et al. 2015

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We report two strategies toward the synthesis of 3-alkyl-4-fluorothiophenes containing straight (hexyl and octyl) and branched (2-ethylhexyl) alkyl groups. We demonstrate that treatment of the dibrominated monomer with 1 equiv of alkyl Grignard reagent leads to the formation of a single regioisomer as a result of the pronounced directing effect of the fluorine group. Polymerization of the resulting species affords highly regioregular poly(3-alkyl-4-fluoro)thiophenes. Comparison of their properties to those of the analogous non-fluorinated polymers shows that backbone fluorination leads to an increase in the polymer ionization potential without a significant change in optical band gap. Fluorination also results in an enhanced tendency to aggregate in solution, which is ascribed to a more co-planar backbone on the basis of Raman and DFT calculations. Average charge carrier mobilities in field-effect transistors are found to increase by up to a factor of 5 for the fluorinated polymers.

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Section: Introductionmentioning

confidence: 99%

Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes

et al. 2015

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Controlling Ambipolar Charge Transport in Isoindigo‐Based Conjugated Polymers by Altering Fluorine Substitution Position for High‐Performance Organic Field‐Effect Transistors

Kim

Park

et al. 2019

Adv Funct Materials

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A molecular design strategy to achieve highly balanced ambipolar charge transport for donor–acceptor (D–A) isoindigo (IIG)‐based copolymer through systematic selection of fluorination positions is reported. To study fluorine substitution site effects on electronic and structural properties, two fluorinated IIG‐based copolymers (PIIG‐iFT2 and PIIG‐oFT2) are synthesized, which contain two fluorine atoms at the bithiophene (T2) inner and outer site and compare them with a nonfluorinated copolymer of IIG and T2 (PIIG‐T2) as the reference polymer. Fluorination at the outer site of T2 in PIIG‐oFT2 polymer effectively lowers molecular energy levels and increases molecular planarity more than fluorination at the T2 inner site. PIIG‐oFT2 organic field‐effect transistors show highly balanced ambipolar mobility, hole mobility (μh)/electron mobility (μe) = 1 by increasing electron mobility, whereas PIIG‐T2 (μh/μe = 9.0) and PIIG‐iFT2 (μh/μe = 2.4) exhibit unbalanced ambipolar transport. The ambipolar complementary‐like inverter is also demonstrated by simple one‐time coating of PIIG‐oFT2 with gain = 21.

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Fluorinated Thiophenes and Their Analogues

Cited by 2 publications

References 182 publications

Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes

Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes

Controlling Ambipolar Charge Transport in Isoindigo‐Based Conjugated Polymers by Altering Fluorine Substitution Position for High‐Performance Organic Field‐Effect Transistors

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