Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 18, Pages 6397-6403Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600579
Keywords
isomers; Janus silsesquioxanes; nanoparticles; NMR spectroscopy
Categories
Funding
- 863 Program [2015AA020941]
- National Natural Science Foundation of China [21474003, 91427304]
- 1000 Plan (Youth)
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A series of regioisomeric Janus-type polyhedral oligomeric silsesquioxanes (POSS) with multiple, mixed surface functional groups has been successfully synthesized based on the cubic T-8-POSS framework in two consecutive thiolene reactions. The first thiol-ene addition of beta-mercaptoethanol leads to a statistical mixture of multi-adducts where the regioisomers of bis-adducts (ortho, meta, and para isomers) can be isolated at synthetically useful quantities by flash column chromatography. Then, the second thiol-ene reaction readily installs a variety of functional groups onto the remaining vinyl groups of each regioisomer, providing an easy access to precisely defined, hetero-bifunctional Janus POSS nano-building blocks. The configurations and structures of the products have been unambiguously proven by using H-1, C-13, and Si-29 NMR spectroscopy as well as MALDI-TOF mass spectrometry.
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