(3Z,3′Z)-3,3′-(Hydrazine-1,2-diylidene)bis(indolin-2-one) as a new electron-acceptor building block for donor–acceptor π-conjugated polymers for organic thin film transistors?

Journal of Materials Chemistry C Pub Date: 2015-03-26 DOI: 10.1039/C5TC00447K

Abstract

(3Z,3′Z)-3,3′-(Hydrazine-1,2-diylidene)bis(indolin-2-one) (HBI) containing an azine linkage is used as a novel amide-based π-conjugated electron-accepting building block for constructing donor–acceptor (D–A) π-polymer semiconductors. Copolymers of HBI and bithiophene are synthesized, which show small optical band gaps (～1.6 eV) and quite low-lying highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels (EHOMO = ?5.6 eV; ELUMO = ?4.0 eV). The spin-coated polymer thin films are highly crystalline with a favoured edge-on lamellar chain packing motif, and exhibit high ambipolar charge transport performance with hole and electron mobilities up to 0.11 and 0.035 cm2 V?1 s?1, respectively.

Graphical abstract: (3Z,3′Z)-3,3′-(Hydrazine-1,2-diylidene)bis(indolin-2-one) as a new electron-acceptor building block for donor–acceptor π-conjugated polymers for organic thin film transistors
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