Molecular Assembly and Gelating Behavior of (l)-Alanine Derivatives.
(l)-amino acid
chiral recognition
low molecular weight organogelator
self-assembly
supermolecular gel
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
11 Jul 2023
11 Jul 2023
Historique:
received:
12
02
2023
medline:
22
4
2023
pubmed:
22
4
2023
entrez:
22
04
2023
Statut:
ppublish
Résumé
In this study, a low-molecular-weight organogelator derived from (l)-amino acids was designed and synthesized. Gelation assays using (l)-amino acid derivatives were performed to confirm the gelation ability, which was found to be high in several compounds. The (l)-alanine derivatives were determined to be excellent gelators, forming good gels even when smaller amounts were added. These results led to a library of amino acid-derived organogelators. In addition, the thermal properties of the (l)-alanine derivatives with high gelation performance were measured. Differential scanning calorimetry measurements revealed that the thermal stability of the gels could be controlled by changing the gelator concentration. The surface states of the obtained gels were observed by field-emission scanning electron microscopy and atomic force microscopy measurements, which confirmed the structure of the self-molecular aggregates. Self-molecular aggregates were observed to be helical or sheet-like, and the gels were constructed by forming aggregates by self-molecular recognition.
Identifiants
pubmed: 37085981
doi: 10.1002/chem.202300455
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300455Subventions
Organisme : The Mitani Foundation for Research and Development
Organisme : Shibuya Science Culture and Sports Foundation
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
D. J. Adams, J. Am. Chem. Soc. 2022, 144, 11047-11053.
E. R. Draper, D. J. Adams, Chem. 2017, 3, 390-410.
R. G. Weiss, J. Am. Chem. Soc. 2014, 136, 7519-7530.
M. George, R. G. Weiss, Acc. Chem. Res. 2006, 39, 489-497.
N. M. Sangeetha, U. Maitra, Chem. Soc. Rev. 2005, 34, 821-836.
Langmuir 2002, 18, 7095-7095.
P. Terech, R. G. Weiss, Chem. Rev. 1997, 97, 3133-3160.
J. H. van Esch, B. L. Feringa, Angew. Chem. Int. Ed. 2000, 39, 2263-2266.
M. Suzuki, K. Hanabusa, Chem. Soc. Rev. 2010, 39, 455-463.
K. Hanabusa, R. Tanaka, M. Suzuki, M. Kimura, H. Shirai, Adv. Mater. 1997, 9, 1095-1097.
K. Hanabusa, M. Yamada, M. Kimura, H. Shirai, Angew. Chem. Int. Ed. Engl. 1996, 35, 1949-1951.
K. Hanabusa, Y. Matsumoto, T. Miki, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1994, 1401-1402.
K. J. C. van Bommel, C. van der Pol, I. Muizebelt, A. Friggeri, A. Heeres, A. Meetsma, B. L. Feringa, J. van Esch, Angew. Chem. Int. Ed. 2004, 43, 1663-1667.
M. de Loos, J. van Esch, R. M. Kellogg, B. L. Feringa, Angew. Chem. Int. Ed. 2001, 40, 613-616.
F. S. Schoonbeek, J. H. van Esch, R. Hulst, R. M. Kellogg, B. L. Feringa, Chem. Eur. J. 2000, 6, 2633-2643.
J. H. van Esch, F. Schoonbeek, M. de Loos, H. Kooijman, A. L. Spek, R. M. Kellogg, B. L. Feringa, Chem. Eur. J. 1999, 5, 937-950.
M. de Loos, J. van Esch, I. Stokroos, R. M. Kellogg, B. L. Feringa, J. Am. Chem. Soc. 1997, 119, 12675-12676.
C. S. Snijder, J. C. de Jong, A. Meetsma, F. van Bolhuis, B. L. Feringa, Chem. Eur. J. 1995, 1, 594-597.
Y. Yamamoto, A. Oyanagi, A. Miyawaki, K. Tomioka, Tetrahedron Lett. 2016, 57, 5889-5892.
T. Sumiyoshi, K. Nishimura, M. Nakano, T. Handa, Y. Miwa, K. Tomioka, J. Am. Chem. Soc. 2003, 125, 12137-12142.
K. Tomioka, T. Sumiyoshi, S. Narui, Y. Nagaoka, A. Iida, Y. Miwa, T. Taga, M. Nakano, T. Handa, J. Am. Chem. Soc. 2001, 123, 11817-11818.
K. Kodama, M. Obata, S. Sugimura, H. Yuhara, T. Hirose, Chem. Eur. J. 2022, e202202692.
B. M. Suresh, Y. Akahori, A. Taghavi, G. Crynen, Q. M. R. Gibaut, Y. Li, M. D. Disney, J. Am. Chem. Soc. 2022, 144, 20815-20824.
E. N. Drew, C. C. Piras, J. Fitremann, D. K. Smith, Chem. Commun. 2022, 58, 11115-11118.
U. Manna, R. Roy, H. K. Datta, P. Dastidar, Chem. Asian J. 2022, 17, e202200660.
F. A. Larik, L. L. Fillbrook, S. S. Nurttila, A. D. Martin, R. P. Kuchel, K. Al Taief, M. Bhadbhade, J. E. Beves, P. Thordarson, Angew. Chem. Int. Ed. 2021, 60, 6764-6770.
C. C. Piras, D. K. Smith, Chem. Eur. J. 2021, 27, 14527-14534.
D. McDowall, M. Walker, M. Vassalli, M. Cantini, N. Khunti, C. J. C. Edwards-Gayle, N. Cowieson, D. J. Adams, Chem. Commun. 2021, 57, 8782-8785.
T. Yan, B. Song, X. Pei, Z. Cui, B. P. Binks, H. Yang, Angew. Chem. Int. Ed. 2020, 59, 637-641.
R. Beniazza, N. Bayo, D. Jardel, R. Rust, B. Mao, T. Divoux, M. Schmutz, F. Castet, G. Raffy, A. Del Guerzo, N. D. McClenaghan, T. Buffeteau, J.-M. Vincent, Chem. Commun. 2020, 56, 8655-8658.
S. Wu, Q. Zhang, Y. Deng, X. Li, Z. Luo, B. Zheng, S. Dong, J. Am. Chem. Soc. 2020, 142, 448-455.
A. D. Ludwig, A. Saint-Jalmes, C. Mériadec, F. Artzner, O. Tasseau, F. Berrée, L. Lemiègre, Chem. Eur. J. 2020, 26, 13927-13934.
Y. Wang, R. M. de Kruijff, M. Lovrak, X. Guo, R. Eelkema, J. H. van Esch, Angew. Chem. Int. Ed. 2019, 58, 3800-3803.
F. M. Menger, K. L. Caran, J. Am. Chem. Soc. 2000, 122, 11679-11691.
K. Hanabusa, H. Shirai, Kobunshi Ronbunshu 1998, 55, 585-594.
X. Chen, Z. Huang, S.-Y. Chen, K. Li, X.-Q. Yu, L. Pu, J. Am. Chem. Soc. 2010, 132, 7297-7299.
M. Qin, Y. Zhang, J. Liu, C. Xing, C. Zhao, X. Dou, C. Feng, Langmuir 2020, 36, 2524-2533.
J. L. Hutter, J. Bechhoefer, Rev. Sci. Instrum. 1993, 64, 1868-1873.