Premium
Janus POSS Based on Mixed [2:6] Octakis‐Adduct Regioisomers
Author(s) -
Han ShuaiYuan,
Wang XiaoMan,
Shao Yu,
Guo QingYun,
Li Yiwen,
Zhang WenBin
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600579
Subject(s) - structural isomer , bifunctional , adduct , chemistry , janus , mass spectrometry , combinatorial chemistry , organic chemistry , chromatography , materials science , catalysis , nanotechnology
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 thiol–ene reactions. The first thiol–ene addition of β‐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 1 H, 13 C, and 29 Si NMR spectroscopy as well as MALDI‐TOF mass spectrometry.