Noncovalent Se···O Conformational Locks for Constructing High-Performing Optoelectronic Conjugated Polymers

Tao Dong, Lei Lv, Linlin Feng, Yu Xia, Wei Deng, Pan Ye, Bei Yang, Shang Ding, Antonio Facchetti*, Huanli Dong, Hui Huang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

79 Scopus citations

Abstract

Noncovalent conformational locks are broadly employed to construct highly planar π-conjugated semiconductors exhibiting substantial charge transport characteristics. However, current chalcogen-based conformational lock strategies for organic semiconductors are limited to S···X (X = O, N, halide) weak interactions. An easily accessible (minimal synthetic steps) and structurally planar selenophene-based building block, 1,2-diethoxy-1,2-bisselenylvinylene (DESVS), with novel Se···O noncovalent conformational locks is designed and synthesized. DESVS unique properties are supported by density functional theory computed electronic structures, single crystal structures, and experimental lattice cohesion metrics. Based on this building block, a new class of stable, structurally planar, and solution-processable conjugated polymers are synthesized and implemented in organic thin-film transistors (TFT) and organic photovoltaic (OPV) cells. DESVS-based polymers exhibit carrier mobilities in air as high as 1.49 cm2 V−1 s−1 (p-type) and 0.65 cm2 V−1 s−1 (n-type) in TFTs, and power conversion efficiency >5% in OPV cells.

Original languageEnglish (US)
Article number1606025
JournalAdvanced Materials
Volume29
Issue number34
DOIs
StatePublished - Sep 13 2017

Keywords

  • Se···O conformational locks
  • conjugated polymers
  • organic photovoltaic cells
  • organic thin-film transistors

ASJC Scopus subject areas

  • Mechanics of Materials
  • Mechanical Engineering
  • General Materials Science

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