Organobridged silsesquioxanes based on cyclobutane diamines: Influence of the stereochemistry on the morphology of the materials

M. Sans; O. Illa; R. M. Ortuño

doi:10.1016/j.tet.2016.04.001

Organobridged silsesquioxanes based on cyclobutane diamines: Influence of the stereochemistry on the morphology of the materials

M. Sans, O. Illa, R. M. Ortuño

Research output: Contribution to journal › Article › Research › peer-review

2 Citations (Scopus)

Abstract

© 2016 Elsevier Ltd. All rights reserved. Two new organobridged silica-based materials have been prepared by sol-gel hydrolysis-condensation of ureido silyl derivatives of an enantiopure chiral trans 1,2-diaminocyclobutane and an achiral meso 1,2-diaminocyclobutane. The influence of the relative and absolute configuration of the stereogenic centers on the morphology and characterization parameters of the resulting materials has been studied. A right-handed helical shape has been observed for the material obtained starting from the meso-cis diamine whereas the material obtained from the chiral trans diamine showed aggregation in the form of platelets. A preliminary experiment of a reduction of a ketone by hydride transfer reaction catalyzed by a rhodium complex embedded in an organic-inorganic hybrid silica is also reported.

Original language	English
Pages (from-to)	2913-2919
Journal	Tetrahedron
Volume	72
Issue number	22
DOIs	https://doi.org/10.1016/j.tet.2016.04.001
Publication status	Published - 2 Jun 2016

Keywords

Bridged silsesquioxane
Chirality
Diaminocyclobutane
Hybrid materials
Sol-gel process

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title = "Organobridged silsesquioxanes based on cyclobutane diamines: Influence of the stereochemistry on the morphology of the materials",

abstract = "{\textcopyright} 2016 Elsevier Ltd. All rights reserved. Two new organobridged silica-based materials have been prepared by sol-gel hydrolysis-condensation of ureido silyl derivatives of an enantiopure chiral trans 1,2-diaminocyclobutane and an achiral meso 1,2-diaminocyclobutane. The influence of the relative and absolute configuration of the stereogenic centers on the morphology and characterization parameters of the resulting materials has been studied. A right-handed helical shape has been observed for the material obtained starting from the meso-cis diamine whereas the material obtained from the chiral trans diamine showed aggregation in the form of platelets. A preliminary experiment of a reduction of a ketone by hydride transfer reaction catalyzed by a rhodium complex embedded in an organic-inorganic hybrid silica is also reported.",

keywords = "Bridged silsesquioxane, Chirality, Diaminocyclobutane, Hybrid materials, Sol-gel process",

author = "M. Sans and O. Illa and Ortu{\~n}o, {R. M.}",

year = "2016",

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TY - JOUR

T1 - Organobridged silsesquioxanes based on cyclobutane diamines: Influence of the stereochemistry on the morphology of the materials

AU - Sans, M.

AU - Illa, O.

AU - Ortuño, R. M.

PY - 2016/6/2

Y1 - 2016/6/2

N2 - © 2016 Elsevier Ltd. All rights reserved. Two new organobridged silica-based materials have been prepared by sol-gel hydrolysis-condensation of ureido silyl derivatives of an enantiopure chiral trans 1,2-diaminocyclobutane and an achiral meso 1,2-diaminocyclobutane. The influence of the relative and absolute configuration of the stereogenic centers on the morphology and characterization parameters of the resulting materials has been studied. A right-handed helical shape has been observed for the material obtained starting from the meso-cis diamine whereas the material obtained from the chiral trans diamine showed aggregation in the form of platelets. A preliminary experiment of a reduction of a ketone by hydride transfer reaction catalyzed by a rhodium complex embedded in an organic-inorganic hybrid silica is also reported.

AB - © 2016 Elsevier Ltd. All rights reserved. Two new organobridged silica-based materials have been prepared by sol-gel hydrolysis-condensation of ureido silyl derivatives of an enantiopure chiral trans 1,2-diaminocyclobutane and an achiral meso 1,2-diaminocyclobutane. The influence of the relative and absolute configuration of the stereogenic centers on the morphology and characterization parameters of the resulting materials has been studied. A right-handed helical shape has been observed for the material obtained starting from the meso-cis diamine whereas the material obtained from the chiral trans diamine showed aggregation in the form of platelets. A preliminary experiment of a reduction of a ketone by hydride transfer reaction catalyzed by a rhodium complex embedded in an organic-inorganic hybrid silica is also reported.

KW - Bridged silsesquioxane

KW - Chirality

KW - Diaminocyclobutane

KW - Hybrid materials

KW - Sol-gel process

U2 - 10.1016/j.tet.2016.04.001

DO - 10.1016/j.tet.2016.04.001

M3 - Article

VL - 72

SP - 2913

EP - 2919

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 22

ER -