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Immobilization of Ethynyl‐π‐Extended Electron Acceptors with Amino‐Terminated SAMs by Catalyst‐Free Click Reaction
Author(s) -
Nakano Kyohei,
Sanematsu Haruki,
Kaji Yumiko,
Takai Atsuro,
Tajima Keisuke
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001750
Subject(s) - catalysis , monolayer , silane , steric effects , chemistry , molecule , surface modification , conjugated system , self assembled monolayer , click chemistry , polymer chemistry , amine gas treating , chemical engineering , photochemistry , organic chemistry , polymer , biochemistry , engineering
Surface modification of SiO 2 using a catalyst‐free quantitative reaction between an amine and an ethynyl‐π‐extended naphthalenediimide was investigated. A post‐reaction method, in which the catalyst‐free reaction was performed at the surface after the formation of amino‐terminated self‐assembled monolayers (SAMs), resulted in dense, uniform modification of the SiO 2 surface with the naphthalenediimide molecules. Both X‐ray reflectivity and angle‐resolved X‐ray photoemission spectroscopy showed consistent results for the layer thickness and density. In contrast, a pre‐reaction method, in which an amino‐silane and the ethynyl‐π‐extended naphthalenediimide reacted first and then formed a SAM, afforded a sparse SAM on the SiO 2 surface, probably due to the steric hindrance of the naphthalenediimide moieties. The in situ decoration of the SiO 2 surface by a catalyst‐free quantitative reaction offers a facile route for modifying surface properties with various π‐conjugated molecules suitable for many applications.