Polyhedral oligomeric silsesquioxane bound fulleropyrrolidines

David J. Clarke; Janis G. Matisons; George R. Simon; Marek Samoc; Anna Samoc

doi:10.1002/aoc.1425

Polyhedral oligomeric silsesquioxane bound fulleropyrrolidines

David J. Clarke, Janis G. Matisons, George R. Simon, Marek Samoc, Anna Samoc

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

8 Citations (Scopus)

Abstract

The first reported examples of polyhedral oligomeric silsesquioxane (POSS) cages containing a fulleropyrrolidine species are reported herein. Monosubstituted POSS-dioxalane species were synthesized through the hydrosilylation of a silyl-dioxalane with mono-vinyl substituted POSS. Subsequent deprotection yielded the desired aldehyde functionality. An alternative synthetic pathway, involving the nucleophilic substitution of mono-benzyl chloride POSS with 4-hydroxybenzaldehyde yielded the desired aldehyde functionality. Each mono-aldehyde POSS was then reacted with N-methylglycine and C60 to yield the desired POSS fulleropyrrolidines. The prepared compounds were characterized by multinuclear NMR, electrospray mass spectrometry, elemental analysis, UV-vis, fluorescence and optical power limiting measurements.

Original language	English
Pages (from-to)	460-465
Number of pages	6
Journal	Applied Organometallic Chemistry
Volume	22
Issue number	8
DOIs	https://doi.org/10.1002/aoc.1425
Publication status	Published - Aug 2008

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title = "Polyhedral oligomeric silsesquioxane bound fulleropyrrolidines",

abstract = "The first reported examples of polyhedral oligomeric silsesquioxane (POSS) cages containing a fulleropyrrolidine species are reported herein. Monosubstituted POSS-dioxalane species were synthesized through the hydrosilylation of a silyl-dioxalane with mono-vinyl substituted POSS. Subsequent deprotection yielded the desired aldehyde functionality. An alternative synthetic pathway, involving the nucleophilic substitution of mono-benzyl chloride POSS with 4-hydroxybenzaldehyde yielded the desired aldehyde functionality. Each mono-aldehyde POSS was then reacted with N-methylglycine and C60 to yield the desired POSS fulleropyrrolidines. The prepared compounds were characterized by multinuclear NMR, electrospray mass spectrometry, elemental analysis, UV-vis, fluorescence and optical power limiting measurements.",

keywords = "Fullerene, Hydrosilylation, Optical limiting, Silsesquioxane",

author = "Clarke, {David J.} and Matisons, {Janis G.} and Simon, {George R.} and Marek Samoc and Anna Samoc",

year = "2008",

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T1 - Polyhedral oligomeric silsesquioxane bound fulleropyrrolidines

AU - Clarke, David J.

AU - Matisons, Janis G.

AU - Simon, George R.

AU - Samoc, Marek

AU - Samoc, Anna

PY - 2008/8

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N2 - The first reported examples of polyhedral oligomeric silsesquioxane (POSS) cages containing a fulleropyrrolidine species are reported herein. Monosubstituted POSS-dioxalane species were synthesized through the hydrosilylation of a silyl-dioxalane with mono-vinyl substituted POSS. Subsequent deprotection yielded the desired aldehyde functionality. An alternative synthetic pathway, involving the nucleophilic substitution of mono-benzyl chloride POSS with 4-hydroxybenzaldehyde yielded the desired aldehyde functionality. Each mono-aldehyde POSS was then reacted with N-methylglycine and C60 to yield the desired POSS fulleropyrrolidines. The prepared compounds were characterized by multinuclear NMR, electrospray mass spectrometry, elemental analysis, UV-vis, fluorescence and optical power limiting measurements.

AB - The first reported examples of polyhedral oligomeric silsesquioxane (POSS) cages containing a fulleropyrrolidine species are reported herein. Monosubstituted POSS-dioxalane species were synthesized through the hydrosilylation of a silyl-dioxalane with mono-vinyl substituted POSS. Subsequent deprotection yielded the desired aldehyde functionality. An alternative synthetic pathway, involving the nucleophilic substitution of mono-benzyl chloride POSS with 4-hydroxybenzaldehyde yielded the desired aldehyde functionality. Each mono-aldehyde POSS was then reacted with N-methylglycine and C60 to yield the desired POSS fulleropyrrolidines. The prepared compounds were characterized by multinuclear NMR, electrospray mass spectrometry, elemental analysis, UV-vis, fluorescence and optical power limiting measurements.

KW - Fullerene

KW - Hydrosilylation

KW - Optical limiting

KW - Silsesquioxane

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U2 - 10.1002/aoc.1425

DO - 10.1002/aoc.1425

M3 - Article

SN - 0268-2605

VL - 22

SP - 460

EP - 465

JO - Applied Organometallic Chemistry

JF - Applied Organometallic Chemistry

IS - 8

ER -

Polyhedral oligomeric silsesquioxane bound fulleropyrrolidines

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