Naphthalene flanked diketopyrrolopyrrole: A new DPP family member and its comparative optoelectronic properties with thiophene- and furan- flanked DPP counterparts

Liu, Qian and Sun, Huabin and Ponnappa, Supreetha Paleyanda and Feron, Krishna and Manzhos, Sergei and Jones, Michael W.M. and Bottle, Steven E. and Bell, John and Noh, Yong-Young and Sonar, Prashant (2019) Naphthalene flanked diketopyrrolopyrrole: A new DPP family member and its comparative optoelectronic properties with thiophene- and furan- flanked DPP counterparts. Organic Electronics, 74. pp. 290-298. ISSN 1566-1199


Abstract

Diketopyrrolopyrrole (DPP) has been one of the most promising building blocks for constructing organic semiconducting materials used in organic field-effect transistors (OFET). As we have known, extended π-conjugated structure can facilitate intermolecular orbital coupling which determines the magnitude of the charge transfer integral and thus the charge transport in devices. What is more, better intramolecular charge transport and intermolecular charge hopping depend on more superior morphology of the conjugated materials in thin film that is influenced by flexible substitutions. Based on the above principles, it is worthy designing and synthesizing fused ring flanked DPP monomers with alkyl chains to exploit their potential use in OFET. In this work, we first synthesized and characterized a new DPP derivative, naphthalene flanked DPP with butyl-octyl side chain (BO-DPPN). When comparing with its thiophene- and furan-flanked DPP analogues using the same common alkyl chain, BO-DPPN appears as most suitable for OFET applications. For example, DSC analysis demonstrates its high degree of crystallinity, UV–Vis spectra show a strong aggregation in solid state, XRD pattern indicates its tight and long-range ordered lamellar packing. As expected, the OFET devices function well when using BO-DPPN directly as active semiconductor and an impressive hole mobility of 0.0126 cm2 V−1 s−1 was observed with a bottom-contact/top-gate architecture using a solution processable approach indicating its promising potential for use in organic electronics.


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Item Type: Article (Commonwealth Reporting Category C)
Refereed: Yes
Item Status: Live Archive
Additional Information: Files associated with this item cannot be displayed due to copyright restrictions.
Faculty/School / Institute/Centre: Current - Research and Innovation Division (12 Jul 2012 -)
Faculty/School / Institute/Centre: Current - Research and Innovation Division (12 Jul 2012 -)
Date Deposited: 16 Sep 2020 23:50
Last Modified: 24 Sep 2020 06:00
Uncontrolled Keywords: Diketopyrrolopyrrole; Naphthalene flanking group; Thiophene and furan DPP analogues; Optoelectronic properties; Organic field-effect transistors
Fields of Research (2008): 09 Engineering > 0912 Materials Engineering > 091299 Materials Engineering not elsewhere classified
Fields of Research (2020): 40 ENGINEERING > 4016 Materials engineering > 401699 Materials engineering not elsewhere classified
Identification Number or DOI: https://doi.org/10.1016/j.orgel.2019.07.017
URI: http://eprints.usq.edu.au/id/eprint/39374

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