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Thiourea as a "Polar Hydrophobic" Hydrogen-Bonding Motif: Application to Highly Durable All-Underwater Adhesion.
Kikkawa, Kohei; Sumiya, Yosuke; Okazawa, Kazuki; Yoshizawa, Kazunari; Itoh, Yoshimitsu; Aida, Takuzo.
Afiliación
  • Kikkawa K; Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.
  • Sumiya Y; Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan.
  • Okazawa K; Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan.
  • Yoshizawa K; Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan.
  • Itoh Y; Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.
  • Aida T; Japan Science and Technology Agency (JST), Precursory Research for Embryonic Science and Technology (PRESTO), 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.
J Am Chem Soc ; 146(30): 21168-21175, 2024 Jul 31.
Article en En | MEDLINE | ID: mdl-39031475
ABSTRACT
Here, we report that, in contrast to urea, thiourea functions as a "polar hydrophobic" hydrogen-bonding motif. Although thiourea is more acidic than urea, thiourea exchanges its N-H protons with water at a rate that is 160 times slower than that for urea at 70 °C. This suggests that thiourea is much less hydrated than urea in an aqueous environment. What led us to this interesting principle was the serendipitous finding that self-healable poly(ether thiourea) adhered strongly to wet glass surfaces. This discovery enabled us to develop an exceptionally durable all-underwater adhesive that can maintain large adhesive strength for over a year even in seawater, simply by mechanically mixing three water-insoluble liquid components on target surfaces. Because thiourea is hydrophobic, its hydrogen-bonding networks within the adhesive structure and at the adhesive-target interface are presumed to be dehydrated. For comparison, a reference adhesive using urea as a representative "polar hydrophilic" hydrogen-bonding motif was durable for less than 4 days in water. Highly durable all-underwater adhesives are needed in various fields of marine engineering and biomedical sciences, but their development has been a major challenge because a hydration layer that spontaneously forms in water always inhibits adhesion.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos