Synthesis of bis[N-(p-aryl)-carbamoyloxy]alkanes as new low-molecular weight organogelators

A series of bis-carbamate-based low-molecular-weight organogelators were synthesized, and their structure-property relationships with respect to their gelation abilities in organic solvents were investigated. The self-aggregation behavior of the thermoreversible organogels was investigated by FTIR, temperature-dependent NMR, and SEM studies. The results revealed that the self-assembly into fibrous structures is driven by hydrogen bonding, ?-? stacking, and hydrophobic interactions. It was found that para-aryl substitution and the number of methylene units connecting two carbamate groups had a significant influence on gelation. The effect of temperature on gel formation was also investigated for all compounds. The most interesting feature was observed for p-hexyl derivative, which gels at -18 °C but not room temperature. Furthermore, thermal properties of the gels were studied by dropping ball experiments and DSC. para-Alkoxyphenyl derivatives were also found to be good organogelators for olive oil, sunflower oil, corn oil, and ethyl laurate, isopropyl myristate, n-butyl palmitate. © 2015 Elsevier Ltd. All rights reserved.

Dergi Adı Tetrahedron
Dergi Cilt Bilgisi 71
Dergi Sayısı 10
Sayfalar 1529 - 1539
Yayın Yılı 2015
Eser Adı
[dc.title]
Synthesis of bis[N-(p-aryl)-carbamoyloxy]alkanes as new low-molecular weight organogelators
Yazar
[dc.contributor.author]
Demir-Ordu Ö.
Yazar
[dc.contributor.author]
Şimşir H.
Yazar
[dc.contributor.author]
Alper K.
Yayın Yılı
[dc.date.issued]
2015
Yayıncı
[dc.publisher]
Elsevier Ltd
Yayın Türü
[dc.type]
article
Özet
[dc.description.abstract]
A series of bis-carbamate-based low-molecular-weight organogelators were synthesized, and their structure-property relationships with respect to their gelation abilities in organic solvents were investigated. The self-aggregation behavior of the thermoreversible organogels was investigated by FTIR, temperature-dependent NMR, and SEM studies. The results revealed that the self-assembly into fibrous structures is driven by hydrogen bonding, ?-? stacking, and hydrophobic interactions. It was found that para-aryl substitution and the number of methylene units connecting two carbamate groups had a significant influence on gelation. The effect of temperature on gel formation was also investigated for all compounds. The most interesting feature was observed for p-hexyl derivative, which gels at -18 °C but not room temperature. Furthermore, thermal properties of the gels were studied by dropping ball experiments and DSC. para-Alkoxyphenyl derivatives were also found to be good organogelators for olive oil, sunflower oil, corn oil, and ethyl laurate, isopropyl myristate, n-butyl palmitate. © 2015 Elsevier Ltd. All rights reserved.
Kayıt Giriş Tarihi
[dc.date.accessioned]
2019-12-23
Açık Erişim Tarihi
[dc.date.available]
2019-12-23
Yayın Dili
[dc.language.iso]
eng
Konu Başlıkları
[dc.subject]
Bis-carbamate
Konu Başlıkları
[dc.subject]
Gelation mechanism
Konu Başlıkları
[dc.subject]
Organogelator
Konu Başlıkları
[dc.subject]
Self-assembly
Konu Başlıkları
[dc.subject]
Structure-property relationship
Haklar
[dc.rights]
info:eu-repo/semantics/closedAccess
ISSN
[dc.identifier.issn]
0040-4020
Sponsor YAYINCI
[dc.description.sponsorship]
109T919
Sponsor YAYINCI
[dc.description.sponsorship]
We thank TUBITAK (The Scientific and Technological Research Council of Turkey, 109T919 ) for providing financial support for this research. We thank Melike Büşra Zorlu, Abant İzzet Baysal University Innovative Food Technologies Development, Application and Research Center for the DSC measurements.
İlk Sayfa Sayısı
[dc.identifier.startpage]
1529
Son Sayfa Sayısı
[dc.identifier.endpage]
1539
Dergi Adı
[dc.relation.journal]
Tetrahedron
Dergi Sayısı
[dc.identifier.issue]
10
Dergi Cilt Bilgisi
[dc.identifier.volume]
71
Tek Biçim Adres
[dc.identifier.uri]
https://dx.doi.org/10.1016/j.tet.2015.01.042
Tek Biçim Adres
[dc.identifier.uri]
https://hdl.handle.net/20.500.12628/7764
Görüntülenme Sayısı ( Şehir )
Görüntülenme Sayısı ( Ülke )
Görüntülenme Sayısı ( Zaman Dağılımı )
Görüntülenme
9
09.12.2022 tarihinden bu yana
İndirme
1
09.12.2022 tarihinden bu yana
Son Erişim Tarihi
26 Aralık 2023 15:47
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Tıklayınız
investigated organogelators gelation temperature Furthermore p-hexyl derivative properties observed feature interesting compounds formation thermal studied isopropyl reserved rights Elsevier palmitate n-butyl myristate laurate dropping sunflower derivatives para-Alkoxyphenyl experiments carbamate effect self-aggregation results studies temperature-dependent organogels
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