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Aggregation-Induced Emission Enhancement from Disilane-Bridged Donor–Acceptor–Donor Luminogens Based on the Triarylamine Functionality

  • Tsukasa Usuki
    Tsukasa Usuki
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
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  • , 
  • Masaki Shimada
    Masaki Shimada
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
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  • , 
  • Yoshinori Yamanoi*
    Yoshinori Yamanoi
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    *E-mail: [email protected]
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    Orcidhttp://orcid.org/0000-0002-6155-2357
  • , 
  • Tatsuhiko Ohto
    Tatsuhiko Ohto
    Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan
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  • , 
  • Hirokazu Tada
    Hirokazu Tada
    Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan
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  • , 
  • Hidetaka Kasai
    Hidetaka Kasai
    Division of Physics, Faculty of Pure and Applied Sciences, Tsukuba Research Center for Interdisciplinary Materials Science (TIMS) & Center for Integrated Research in Fundamental Science and Engineering (CiRfSE), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan
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  • , 
  • Eiji Nishibori
    Eiji Nishibori
    Division of Physics, Faculty of Pure and Applied Sciences, Tsukuba Research Center for Interdisciplinary Materials Science (TIMS) & Center for Integrated Research in Fundamental Science and Engineering (CiRfSE), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan
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  • , and 
  • Hiroshi Nishihara*
    Hiroshi Nishihara
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    *E-mail: [email protected]
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Cite this: ACS Appl. Mater. Interfaces 2018, 10, 15, 12164–12172
Publication Date (Web):January 9, 2018
https://doi.org/10.1021/acsami.7b14802
Copyright © 2018 American Chemical Society
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    Abstract

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    Six novel donor–acceptor–donor organic dyes containing a Si–Si moiety based on triarylamine functionalities as donor units were prepared by Pd-catalyzed arylation of hydrosilanes. Their photophysical, electrochemical, and structural properties were studied in detail. Most of the compounds showed attractive photoluminescence (PL) and electrochemical properties both in solution and in the solid state because of intramolecular charge transfer (ICT), suggesting these compounds could be useful for electroluminescence (EL) applications. The aggregation-induced emission enhancement (AIEE) characteristics of 1 and 3 were examined in mixed water/THF solutions. The fluorescence intensity in THF/water was stronger in the solution with the highest ratio of water because of the suppression of molecular vibration and rotation in the aggregated state. Single-crystal X-ray diffraction of 4 showed that the reduction of intermolecular π–π interaction led to intense emission in the solid state and restricted intramolecular rotation of the donor and acceptor moieties, thereby indicating that the intense emission in the solid state is due to AIEE. An electroluminescence device employing 1 as an emitter exhibited an external quantum efficiency of up to 0.65% with green light emission. The emission comes solely from 1 because the EL spectrum is identical to that of the PL of 1. The observed luminescence was sufficiently bright for application in practical devices. Theoretical calculations and electrochemical measurements were carried out to aid in understanding the optical and electrochemical properties of these molecules.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acsami.7b14802.

    • Optical properties of 1–6 in toluene and acetone, relative fluorescence quantum yields of 1–6 in dichloromethane, UV–vis and FL spectra of 1–6, fluorescence spectrum of 1 and 3 in dichloromethane at various concentration, fluorescence spectrum of 1 in PMMA, crystallographic data of 4, cyclic voltammogram of 1, thermal stability of 1–6, energy diagram of OLED, theoretical calculations of 1–6, OLED characteristics, copies of 1H & 13C NMR of 1–6 (PDF)

    • Crystallographic information file for C56H62N4O4SSi4 (CIF)

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