Issue 17, 2015

(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

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

Supplementary files

Article information

Article type
Paper
Submitted
14 Feb 2015
Accepted
26 Mar 2015
First published
26 Mar 2015

J. Mater. Chem. C, 2015,3, 4464-4470

Author version available

(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

W. Hong, C. Guo, B. Sun and Y. Li, J. Mater. Chem. C, 2015, 3, 4464 DOI: 10.1039/C5TC00447K

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