Effect of Alkyl Chain Length of N-Alkyl-N'-(2-benzylphenyl)ureas on Gelation.

alkyl group gels rheology self-assembly urea

Journal

Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643

Informations de publication

Date de publication:
05 Jul 2021
Historique:
revised: 17 05 2021
received: 23 04 2021
pubmed: 20 5 2021
medline: 20 5 2021
entrez: 19 5 2021
Statut: ppublish

Résumé

Urea derivatives that were substituted with a 2-benzylphenyl group and an alkyl group functioned as low molecular weight gelators for various organic solvents and ionic liquids. Urea derivatives with long alkyl chains were effective for the gelation of polar solvents. However, they were not suitable for the gelation of non-polar solvents, whereas urea derivatives with short alkyl chains were effective. Ionic liquids were similar to polar solvents in that urea derivatives with long alkyl chains were the most effective gelators. The physical properties of the formed supramolecular gels were analyzed by dynamic viscoelasticity measurements using a rheometer.

Identifiants

pubmed: 34008323
doi: 10.1002/asia.202100433
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

1750-1755

Subventions

Organisme : Grant-in-aid for the Scientific Research
ID : 20K06977
Organisme : Grant-in-aid for the Scientific Research
ID : 17H06374
Organisme : Grant-in-aid for the Scientific Research
ID : 21K06485
Organisme : Japan Society for the Promotion of Science
Organisme : Ministry of Education, Culture, Sports, Science and Technology
Organisme : NOVARTIS Foundation

Informations de copyright

© 2021 Wiley-VCH GmbH.

Références

S. Seiffert, J. Sprakel, Chem. Soc. Rev. 2012, 41, 909-930.
Y. Lan, M. G. Corradini, R. G. Weiss, S. R. Raghavan, M. A. Rogers, Chem. Soc. Rev. 2015, 44, 6035-6058.
H. Maeda, Chem. Eur. J. 2008, 14, 11274-11282.
Z. Yang, G. Liang, B. Xu, Acc. Chem. Res. 2008, 41, 315-326.
G. O. Lloyd, J. W. Steed, Nat. Chem. 2009, 1, 437-442.
N. Falcone, H. B. Kraatz, Chem. Eur. J. 2018, 24, 14316-14328.
T. Kato, Y. Hirai, S. Nakaso, M. Moriyama, Chem. Soc. Rev. 2007, 36, 1857-1867.
A. R. Hirst, B. Escuder, J. F. Miravet, D. K. Smith, Angew. Chem. 2008, 120, 8122-8139;
Angew. Chem. Int. Ed. 2008, 47, 8002-8018.
X. Du, J. Zhou, J. Shi, B. Xu, Chem. Rev. 2015, 115, 13165-13307.
B. O. Okesola, D. K. Smith, Chem. Soc. Rev. 2016, 45, 4226-4251.
J. H. van Esch, B. L. Feringa, Angew. Chem. 2000, 112, 2351-2354;
Angew. Chem. Int. Ed. 2000, 39, 2263-2266.
A. Dawn, T. Shiraki, S. Haraguchi, S. Tamaru, S. Shinkai, Chem. Asian J. 2011, 6, 266-282.
S. S. Babu, V. K. Praveen, A. Ajayaghosh, Chem. Rev. 2014, 114, 1973-2129.
R. G. Weiss, J. Am. Chem. Soc. 2014, 136, 7519-7530.
M. Yamanaka, J. Inclusion Phenom. Macrocyclic Chem. 2013, 77, 33-48.
M. Yokoya, S. Kimura, M. Yamanaka, Chem. Eur. J. 2021, 27, 5601-5614.
D. M. Wood, B. W. Greenland, A. L. Acton, F. Rodríguez-Llansola, C. A. Murray, C. J. Cardin, J. F. Miravet, B. Escuder, I. W. Hamley, W. Hayes, Chem. Eur. J. 2012, 18, 2692-2699.
E. M. Schön, E. Marqués-López, R. P. Herrera, C. Alemán, D. Diaz Diaz, Chem. Eur. J. 2014, 20, 10720-10731.
A. E. Hooper, S. R. Kennedy, C. D. Jones, J. W. Steed, Chem. Commun. 2016, 52, 198-201.
F. Piana, D. H. Case, S. M. Ramalhete, G. Pileio, M. Facciotti, G. M. Day, Y. Z. Khimyak, J. Angulo, R. C. Brown, P. A. Gale, Soft Matter 2016, 12, 4034-4043.
S. Akama, T. Maki, M. Yamanaka, Chem. Commun. 2018, 54, 8814-8817.
M. George, G. Tan, V. T. John, R. G. Weiss, Chem. Eur. J. 2005, 11, 3243-3254.
H. Yang, T. Yi, Z. Zhou, Y. Zhou, J. Wu, M. Xu, F. Li, C. Huang, Langmuir 2007, 23, 8224-8230.
J. W. Liu, Y. Yang, C. F. Chen, J. T. Ma, Langmuir 2010, 26, 9040-9044.
D. D. Prabhu, A. P. Sivadas, S. Das, J. Mater. Chem. C 2014, 2, 7039-7046.
L. Ji, G. Ouyang, M. Liu, Langmuir 2017, 33, 12419-12426.
A. Sandeep, V. K. Praeen, D. S. S. Rao, S. K. Prasad, A. Ajayaghosh, ACS Omega 2018, 3, 4392-4399.
S. Kondo, J. Masuda, T. Komiyama, N. Yasuda, H. Takaya, M. Yamanaka, Chem. Eur. J. 2019, 25, 16201-16206.
N. Kimizuka, T. Nakashima, Langmuir 2001, 17, 6759-6761.
J. Le Bideau, L. Viau, A. Vioux, Chem. Soc. Rev. 2011, 40, 907-925.
A. Dawn, H. Kumari, Chem. Eur. J. 2018, 24, 762-776.
J. Takeshita, Y. Hasegawa, K. Yanai, A. Yamamoto, A. Ishii, M. Hasegawa, M. Yamanaka, Chem. Asian J. 2017, 12, 2029-2032.

Auteurs

Tomoki Komiyama (T)

Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo, 204-8588, Japan.
Department of Chemistry, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan.

Yoko Harada (Y)

Department of Chemistry, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan.

Takayuki Hase (T)

Department of Chemistry, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan.

Sota Mori (S)

Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo, 204-8588, Japan.

Shinya Kimura (S)

Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo, 204-8588, Japan.

Masashi Yokoya (M)

Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo, 204-8588, Japan.

Masamichi Yamanaka (M)

Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo, 204-8588, Japan.

Classifications MeSH