Influence of Molecular Symmetry and Terminal Substituents on the Morphology and OFET Characteristics of S,N-Heteropentacenes

Yi-Fan Huang, Chin-Lung Chung, Suhendro Purbo Prakoso, Guan-Ting Ciou, Chun-Kai Wang, Yi-Sheng Chen, Bo-Han Lai, Ken-Tsung Wong, Chien-Lung Wang

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Many heteroacenes have been extensively studied to improve device performances; however, the morphological effects stemmed from the chemical modification on a multiscale remain less explored. In this research, five axisymmetric S,Nheteropentacenes (DTPT, DTPT-Ph, DTPT-CN, DTPT-PYCN, and DTPT-BTCN) are studied to reveal the influences of molecular symmetry and end- capping substituents on the structure-property relationship, the thermal stability, crystallization behavior, film morphology, and OFET performance. Phase behavior was probed by differential scanning calorimetry (DSC), while the quality of the crystal array and structural details was investigated by optical microscopy (OM) and grazing-incidence wide-angle X-ray scattering (GIWAXS). The analytic results reveal that (1) the parent axisymmetric S,N-heteropentacene, DTPT, is hard to crystallize, which hinders the preparation of high-quality crystal arrays for the OFET application. (2) The incorporation of pi-conjugated electron-withdrawing (pi-EW) endcaps that provide extended conjugation length and enhanced molecular polarity is required to form oriented crystal arrays to deliver reasonable OFET characteristics. (3) The pi-EW endcaps with conformational freedom, such as -BTCN, due to the asymmetric feature of benzothiadiazole (BT), can hinder bulk phase crystallization and cause conformational disorder in the crystal array. Hence, the tradeoff of introducing the end-substituents to reinforce the poor crystalline nature of S,N-heteroacenes should be carefully considered.

Original languageEnglish
Pages (from-to)40572-40580
Number of pages9
JournalACS applied materials & interfaces
Issue number36
StatePublished - 9 Sep 2020


  • S,N-heteroacenes
  • organic field-effect transistor
  • conformational disorder
  • end-functionalized
  • electron-withdrawing group

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