Colloid and Polymer Science

, Volume 296, Issue 6, pp 1017–1028 | Cite as

Design and synthesis of multi-functional silsesquioxane nanoparticles having two distinct optoelectronic functionalities

  • Yusuke Sasaki
  • Shun Shibasaki
  • Chen-Tsyr Lo
  • Kazuhiro Nakabayashi
  • Hideharu Mori
Original Contribution


Multi-functional silsesquioxane nanoparticles (SQ-NPs) having two distinct optoelectronic functionalities on a single arm were prepared using a thiol-epoxy click reaction followed by esterification. The epoxy-functionalized SQ-NPs were prepared from commercially available (3-glycidyloxypropyl)triethoxysilane and were employed in the thiol-epoxy click reaction to introduce aromatic and heterocyclic thiol compounds, such as naphthalenethiol, 2-mercapto-1-methylimidazole, and 4,5-diphenyl-2-oxazolethiol. The resulting hydroxyl-functionalized SQ-NPs were further functionalized via esterification to incorporate a second functional group. The X-ray diffraction (XRD), size-exclusion chromatography (SEC), and scanning force microscopy (SFM) results indicated the formation of SQ-NPs (< 5 nm) with relatively narrow size distributions and no aggregation. Multi-functional SQ-NPs containing peripheral electron-accepting benzothiazole moieties were also synthesized using 2-mercaptobenzothiazole. The resulting SQ-NPs showed good solubility, high refractive indices (1.55–1.62), high thermal stability (Td5 > 300 °C), and characteristic optoelectronic properties with a wide range of Stokes shifts (5200–12,000 cm−1). The optoelectronic properties of the multi-functional SQ-NPs could be controlled by modifying the structure of the two distinct functional groups, which could be easily tuned by varying the structure of the thiol compounds and acid chloride derivatives in the feed.


Silsesquioxane Multi-functional nanoparticles Optoelectronic functionalities Organic-inorganic hybrid 



There was no financial support obtained for the reported work.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

396_2018_4320_MOESM1_ESM.pdf (1.1 mb)
ESM 1 (PDF 1117 kb)


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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • Yusuke Sasaki
    • 1
  • Shun Shibasaki
    • 2
  • Chen-Tsyr Lo
    • 1
  • Kazuhiro Nakabayashi
    • 1
    • 2
  • Hideharu Mori
    • 1
    • 2
  1. 1.Department of Organic Materials Science, Graduate School of Organic Materials ScienceYamagata UniversityYonezawaJapan
  2. 2.Department of Polymer Science and Engineering, Graduate School of Science and EngineeringYamagata UniversityYonezawaJapan

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