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Molecules 2015, 20(9), 17362-17377; doi:10.3390/molecules200917362

Isoindigo-Based Small Molecules with Varied Donor Components for Solution-Processable Organic Field Effect Transistor Devices

1
School of Applied Sciences, RMIT University, GPO Box 2476, Melbourne Victoria 3001, Australia
2
Institute of Materials Research and Engineering (IMRE), A
3
Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville Victoria 3052, Australia
4
CSIRO Manufacturing, Virtual Nanoscience Lab, Parkville Victoria 3052, Australia
5
School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, GPO Box 2434, Brisbane QLD 4001, Australia
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 3 August 2015 / Revised: 15 September 2015 / Accepted: 15 September 2015 / Published: 18 September 2015
(This article belongs to the Section Molecular Diversity)
View Full-Text   |   Download PDF [7400 KB, uploaded 21 September 2015]   |  

Abstract

Two solution-processable small organic molecules, (E)-6,6′-bis(4-(diphenylamino)phenyl)-1,1′-bis(2-ethylhexyl)-(3,3′-biindolinylidene)-2,2′-dione (coded as S10) and (E)-6,6′-di(9H-carbazol-9-yl)-1,1′-bis(2-ethylhexyl)-(3,3′-biindolinylidene)-2,2′-dione (coded as S11) were successfully designed, synthesized and fully characterized. S10 and S11 are based on a donor-acceptor-donor structural motif and contain a common electron accepting moiety, isoindigo, along with different electron donating functionalities, triphenylamine and carbazole, respectively. Ultraviolet-visible absorption spectra revealed that the use of triphenylamine donor functionality resulted in an enhanced intramolecular charge transfer transition and reduction of optical band gap, when compared with its carbazole analogue. Both of these materials were designed to be donor semiconducting components, exerted excellent solubility in common organic solvents, showed excellent thermal stability, and their promising optoelectronic properties encouraged us to scrutinize charge-carrier mobilities using solution-processable organic field effect transistors. Hole mobilities of the order of 2.2 × 10−4 cm2/Vs and 7.8 × 10−3 cm2/Vs were measured using S10 and S11 as active materials, respectively. View Full-Text
Keywords: isoindigo; solution-processable; organic field effect transistors; donor-acceptor-donor; carbazole; triphenylamine isoindigo; solution-processable; organic field effect transistors; donor-acceptor-donor; carbazole; triphenylamine
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Patil, H.; Chang, J.; Gupta, A.; Bilic, A.; Wu, J.; Sonar, P.; Bhosale, S.V. Isoindigo-Based Small Molecules with Varied Donor Components for Solution-Processable Organic Field Effect Transistor Devices. Molecules 2015, 20, 17362-17377.

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