Publication

A Versatile Synthetic Path to Thiol Containing Polysiloxanes

2016
Journal Articles

Abstract

A synthetic strategy to polydimethylsiloxanes and polymethylsiloxanes containing thiol functions as end- or side-groups, respectively, is presented. Such polymers are important starting materials for elastomeric networks and postpolymerization modifications. The synthesis starts either with vinyl end-functionalized polydimethylsiloxanes or with polymethylvinylsiloxanes. The vinyl groups are reacted either with thioacetic acid or with a thioacetic acid/butanethiol mixture via a UV-initiated thiol-ene reaction to form the respective thioester quantitatively within few minutes. The thioesters are subsequently deprotected to the respective thiols by reduction with LiAlH4. The resulting thiol containing polysiloxanes can be used for the formation of networks or another functionalization. (C) 2016 Wiley Periodicals, Inc.

Official source

https://infoscience.epfl.ch/entities/publication/b04eb3d4-bd0d-4fd9-8944-9049f2113caa

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2016
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/b04eb3d4-bd0d-4fd9-8944-9049f2113caa

About this result

Related concepts (24)

Thiol

In organic chemistry, a thiol ('θaɪɒl; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols (that is, sulfur takes the place of oxygen in the hydroxyl () group of an alcohol), and the word is a blend of "thio-" with "alcohol". Many thiols have strong odors resembling that of garlic or rotten eggs.

Disulfide

In biochemistry, a disulfide (or disulphide in British English) refers to a functional group with the structure . The linkage is also called an SS-bond or sometimes a disulfide bridge and is usually derived by the coupling of two thiol groups. In biology, disulfide bridges formed between thiol groups in two cysteine residues are an important component of the secondary and tertiary structure of proteins. Persulfide usually refers to compounds. In inorganic chemistry disulfide usually refers to the corresponding anion S22− (−S−S−).

Thioester

In organic chemistry, thioesters are organosulfur compounds with the molecular structure . They are analogous to carboxylate esters () with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix. They are the product of esterification of a carboxylic acid () with a thiol (). In biochemistry, the best-known thioesters are derivatives of coenzyme A, e.g., acetyl-CoA. The R and R' represent organyl groups, or H in the case of R.

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A Versatile Synthetic Path to Thiol Containing Polysiloxanes

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