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Naphthalimide End Capped Anthraquinone Based Solution-Processable n-Channel Organic Semiconductors: Effect of Alkyl Chain Engineering on Charge Transport

Abstract

Herein, we are reporting the synthesis, characterization and organic field effect transistor characteristics of a new class of 1,8-naphthalimide and 9,10-anthraquinone strong electron withdrawing group based n-channel small molecule semiconductors with different branched alkyl chain length, namely NAI-ANQ-NAI (BO), NAI-ANQ-NAI (HD), and NAI-ANQ-NAI (DT). All three small molecules exhibit different solubility behavior based on their alkyl chain length in a common organic solvent. NAI-ANQ-NAI (BO), NAI-ANQ-NAI (HD), and NAI-ANQ-NAI (DT) show quite deep LUMO energy levels (around -4.2 eV) which is promising for better air-stable electron transport. Under ambient atmosphere, we found that electron mobilities of solution-processed thin-film transistors based on these small molecules exhibited different trends of thermal annealing effect in the range of 140-200 oC. For the NAI-ANQ-NAI (BO) and NAI-ANQ-NAI (HD), when annealing temperature increases from 140 to 200 oC, there is significant improvement of electron mobility from 5.91 x 10-3 to 4.18 x 10-2 cm2V-1s-1 and from 8.39 x 10-3 to 3.13 x 10-2 cm2V-1s-1, respectively. Meanwhile, NAI-ANQ-NAI (DT) demonstrates the slight improvement of mobility from 1.47 x 10-2 to 3.60 x 10-2 cm2V-1s-1. The spin-coated films of these materials exhibited quite smooth and uniform morphology although these are small molecules and crystalline. These results clearly demonstrate that the fused anthraquinone and naphthalimide are potential functional moieties for constructing low cost solution processable electron transporting materials for organic and printed electronics.

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Publication details

The article was received on 13 Nov 2017, accepted on 14 Feb 2018 and first published on 14 Feb 2018


Article type: Paper
DOI: 10.1039/C7TC05172G
Citation: J. Mater. Chem. C, 2018, Accepted Manuscript
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    Naphthalimide End Capped Anthraquinone Based Solution-Processable n-Channel Organic Semiconductors: Effect of Alkyl Chain Engineering on Charge Transport

    P. M. Sonar, T. T. Do, Y. Takeda, S. Tokito, J. M. Bell and S. Manzhos, J. Mater. Chem. C, 2018, Accepted Manuscript , DOI: 10.1039/C7TC05172G

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