N-Heteroheptacenequinone and N-heterononacenequinone : synthesis, physical properties, crystal structures and photoelectrochemical behaviors

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

  • Junbo Li
  • Jianwei Miao
  • Guankui Long
  • Jing Zhang
  • Yongxin Li
  • Rakesh Ganguly
  • Yang Zhao
  • Yi Liu

Detail(s)

Original languageEnglish
Pages (from-to)9877-9884
Journal / PublicationJournal of Materials Chemistry C
Volume3
Issue number38
Online published27 Aug 2015
Publication statusPublished - 14 Oct 2015
Externally publishedYes

Abstract

N-heteroquinones with both quinone and pyrazine as electron-withdrawing moieties can be potential candidates for n-type organic semiconductor materials. Here, two novel soluble N-heteroquinones: 5,9,14,18-tetra-((triisopropylsilyl)ethynyl)-6,8,15,17-tetraazaheptacene-7,16-dione (TAHD) and 6,10,17,21-tetra-((triisopropylsilyl)ethynyl)-7,9,18,20-tetraazanonacene-8,19-dione (TAND) with different lengths have been synthesized and their structures were fully characterized by 1H NMR, 13C NMR, HRMS and single crystal analysis. Our studies showed that the shorter TAHD molecules are planar in the solid state without intermolecular π-π stacking and the main force to stabilize the packing is the C-H-π interaction between (triisopropylsilyl)ethynyl (TIPS) groups and the backbones. Differently, the larger TAND molecules show slightly twisted structures with the anthracene units bent down and up on the two sites and the dihedral angle between the quinone unit and the anthracene unit is 6.7°. Meanwhile, TAND molecules adopt face-to-face two-dimensional (2D) brickwork arrangement, and the distances between π planes are 3.63 and 3.38 nm, respectively, suggesting the existence of π-π interactions. The visible-light-driven photoelectrochemical behaviors showed that both TAHD and TAND are n-type semiconductors. However, TAHD shows unstable photovoltage response and lower photocurrent due to the absence of π-π interaction while TAND shows stable photovoltage response and a relatively high photocurrent. Our results suggested that the length of the linear N-heteroquinones has large effects on their physical properties, crystal packing and photoelectrochemical behaviors. © The Royal Society of Chemistry 2015.

Citation Format(s)

N-Heteroheptacenequinone and N-heterononacenequinone: synthesis, physical properties, crystal structures and photoelectrochemical behaviors. / Li, Junbo; Miao, Jianwei; Long, Guankui et al.
In: Journal of Materials Chemistry C, Vol. 3, No. 38, 14.10.2015, p. 9877-9884.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review