Hwang, Hye-Jeong Choi, Inseong Kim, Young-Jin Kim, Young-Kwan Yeo, Woon-Seok 2024-01-19T21:02:38Z 2024-01-19T21:02:38Z 2021-09-04 2019-01-01 0927-7765 https://pubs.kist.re.kr/handle/201004/120492 Various phenol-containing molecules such as flavonoids have a wide range of biological effects including anticancer, antimicrobial, and anti-inflammatory properties, and, therefore, they have become subjects of active research for various medicinal and biological applications. To construct applicable materials incorporated with phenol-containing molecules, strategies for immobilization of phenol-containing molecules on solid substrates are required. Although several immobilization methods have been devised and reported, mostly harnessing phenol functionality, however, development of a general immobilization method has been hampered due to its complicated chemical reactions and low reaction yields on surfaces. Furthermore, the use of phenol as a reaction center may compromise the biological activity of phenol-containing molecules. Here, we describe a simple, fast, and reliable method for the surface immobilization of phenol-containing molecules by introducing chemical functional groups, carboxylic acid, thiol, and azide, while maintaining phenol functionality by way of the Mannich-type condensation reaction. We examined the chemical functionalization of naphthol, tyrosine, and flavanone and their immobilization to the self-assembled monolayers on gold via various surface chemistries: the carbodiimide coupling reaction, Michael addition, and the 'click' reaction. We strongly believe our method can be a general and practical platform for immobilization of various phenol-containing molecules on surfaces of various materials. English ELSEVIER SCIENCE BV MASS-SPECTROMETRY Immobilization of phenol-containing molecules on self-assembled monolayers on gold via surface chemistry Article 10.1016/j.colsurfb.2018.09.054 1 COLLOIDS AND SURFACES B-BIOINTERFACES, v.173, pp.164 - 170 COLLOIDS AND SURFACES B-BIOINTERFACES 173 164 170 scie scopus 000454377300020 2-s2.0-85054168545 Biophysics Chemistry, Physical Materials Science, Biomaterials Biophysics Chemistry Materials Science Article MASS-SPECTROMETRY Immobilization Mannich reaction Phenol-containing molecules Self-assembled monolayers Surface chemistry