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Effect of N-Methylation on Dopamine Surface Chemistry.
Kim, Yejin; You, Ahrom; Kim, Dahee; Bisht, Himani; Heo, Yoonji; Hong, Daewha; Kim, Min; Kang, Sung Min.
Afiliación
  • Kim Y; Department of Chemistry, Chungbuk National University, Cheongju 28644, Chungbuk, Republic of Korea.
  • You A; Department of Chemistry, Chungbuk National University, Cheongju 28644, Chungbuk, Republic of Korea.
  • Kim D; Department of Chemistry, Chungbuk National University, Cheongju 28644, Chungbuk, Republic of Korea.
  • Bisht H; Department of Chemistry and Chemistry Institute of Functional Materials, Pusan National University, Busan 46241, Republic of Korea.
  • Heo Y; Department of Chemistry, Chungbuk National University, Cheongju 28644, Chungbuk, Republic of Korea.
  • Hong D; Department of Chemistry and Chemistry Institute of Functional Materials, Pusan National University, Busan 46241, Republic of Korea.
  • Kim M; Department of Chemistry, Chungbuk National University, Cheongju 28644, Chungbuk, Republic of Korea.
  • Kang SM; Department of Chemistry, Chungbuk National University, Cheongju 28644, Chungbuk, Republic of Korea.
Langmuir ; 38(20): 6404-6410, 2022 05 24.
Article en En | MEDLINE | ID: mdl-35574836
Dopamine (DA) surface chemistry has received significant attention because of its applicability in a wide range of research fields and the ability to graft functional molecules onto numerous solid surfaces. Various DA derivatives have been newly synthesized to identify key factors affecting the coating efficiency and to advance the coating system development. The oxidation of catechol into quinone followed by internal cyclization via the nucleophilic attack of primary amine is crucial for DA-based surface coating. Thus, it is expected that the amine group's nucleophilicity control directly affects the coating efficiency. However, it has not been systematically investigated, and most studies have been conducted with the focus on the transformation of amines into amides, despite such approaches decreasing the coating efficiency; the nitrogen in amides is less nucleophilic than that in free amines. In this study, we investigated the effect of N-alkylation on dopamine surface chemistry. N,N-Dimethyldopamine (DMDA) was newly synthesized, and the coating efficiency was systematically compared with DA and N-methyldopamine (MDA). DA N-monomethylation improved the coating rate by increasing the nitrogen nucleophilicity, whereas N,N-dimethylation dramatically decreased the DA surface coating property. In addition, MDA remained capable of universal surface coating and secondary reactions using the surface catechols. This study provides opportunities for developing coating materials with advanced functions and an improved coating rate.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Dopamina / Aminas Tipo de estudio: Prognostic_studies Idioma: En Revista: Langmuir Asunto de la revista: QUIMICA Año: 2022 Tipo del documento: Article Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Dopamina / Aminas Tipo de estudio: Prognostic_studies Idioma: En Revista: Langmuir Asunto de la revista: QUIMICA Año: 2022 Tipo del documento: Article Pais de publicación: Estados Unidos