Donor/Acceptor Segregated π-Stacking Arrays by Use of Shish-Kebab-Type Polymeric Backbones: Highly Conductive Discotic Blends of Phthalocyaninatopolysiloxanes and Perylenediimides

Tsuneaki Sakurai, Satoru Yoneda, Shugo Sakaguchi, Kenichi Kato, Masaki Takata, Shu Seki

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Construction of large-area electron donor-acceptor (D-A) interfaces and hole/electron pathways is important for photoconducting and photovoltaic functions. Although blends of D- and A-type discotic π-systems have a possibility to realize one-dimensional charge carrier pathways as well as heterointerfaces, D-A segregated structures are difficult to develop by self-assembly because they are entropically unfavored structures. Here we report the use of shish-kebab-type hole-transporting discotic columns fixed by a self-threading polysiloxane chain and approach to such segregated nanostructures. Electron-donor/acceptor blends of soluble phthalocyaninatopolysiloxanes (Poly-SiPcs) and perylenedicarboximides (PDIs) were prepared, and their photoconductive property was investigated. Although Poly-SiPc1 shows a photoinduced charge separation with PDI1 analogous to the corresponding monomeric phthalocyanines (SiPc1 and H2Pc1), the Poly-SiPc1/PDI1 system displays a remarkably larger photoconductivity than SiPc1/PDI1 and H2Pc1/PDI1, which mostly results from the presence of hole-transporting pathways with the mobility μh,1D ∼ 0.1 cm2 V-1 s-1 in Poly-SiPc1 along the polysiloxane covalent bonds even upon mixing with PDI1. When π-stackable PDI2 is used instead of PDI1, X-ray diffraction analysis disclosed obvious signs of π-stacking periodicities for both Pc and PDI planes in the mixture, indicating the presence of donor-acceptor segregated domains of columnar structures. As a result, photoexcitation of Poly-SiPc1/PDI2 generates highly mobile holes and electrons, leading to the observation of a much larger conductivity.

Original languageEnglish
Pages (from-to)9265-9275
Number of pages11
JournalMacromolecules
Volume50
Issue number23
DOIs
Publication statusPublished - 2017 Dec 12
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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