Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of .gamma.-cyclodextrin

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389013%3A_____%2F17%3A00482139" target="_blank" >RIV/61389013:_____/17:00482139 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11310/17:10367090 RIV/00216208:11110/17:10367090

Result on the web

<a href="http://dx.doi.org/10.3762/bjoc.13.248" target="_blank" >http://dx.doi.org/10.3762/bjoc.13.248</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3762/bjoc.13.248" target="_blank" >10.3762/bjoc.13.248</a>

Result language

angličtina

Original language name

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of .gamma.-cyclodextrin

Original language description

Monosubstituted derivatives of gamma-cyclodextrin (gamma-CD) are suitable building blocks for supramolecular polymers, and can also serve as precursors for the synthesis of other regioselectively monosubstituted gamma-CD derivatives. We prepared a set of monosubstituted 2I-O-, 3I-O-, and 6I-O-(3-(naphthalen-2-yl)prop-2-en-1-yl) derivatives of gamma-CD using two different methods. A key step of the first synthetic procedure is a cross-metathesis between previously described regioisomers of mono-O-allyl derivatives of gamma-CD and 2-vinylnaphthalene which gives yields of about 16-25% (2-5% starting from gamma-CD). To increase the overall yields, we have developed another method, based on a direct alkylation of gamma-CD with 3-(naphthalen-2-yl)allyl chloride as the alkylating reagent. Highly regioselective reaction conditions, which differ for each regioisomer in a used base, gave the monosubstituted isomers in yields between 12-19%. Supramolecular properties of these derivatives were studied by DLS, ITC, NMR, and Cryo-TEM.

Czech name

—

Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10404 - Polymer science

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Beilstein Journal of Organic Chemistry

ISSN

1860-5397

e-ISSN

—

Volume of the periodical

13

Issue of the periodical within the volume

27 November

Country of publishing house

DE - GERMANY

Number of pages

12

Pages from-to

2509-2520

UT code for WoS article

000416340800001

EID of the result in the Scopus database

2-s2.0-85035751262