Maleimide-activated aryl diazonium salts for electrode surface functionalization with biological and redox-active molecules

Langmuir : the ACS Journal of Surfaces and Colloids
Jason C HarperSusan M Brozik

Abstract

A versatile and simple method is introduced for formation of maleimide-functionalized surfaces using maleimide-activated aryl diazonium salts. We show for the first time electrodeposition of N-(4-diazophenyl)maleimide tetrafluoroborate on gold and carbon electrodes which was characterized via voltammetry, grazing angle FTIR, and ellipsometry. Electrodeposition conditions were used to control film thickness and yielded submonolayer-to-multilayer grafting. The resulting phenylmaleimide surfaces served as effective coupling agents for electrode functionalization with ferrocene and the redox-active protein cytochrome c. The utility of phenylmaleimide diazonium toward formation of a diazonium-activated conjugate, followed by direct electrodeposition of the diazonium-modified DNA onto the electrode surface, was also demonstrated. Effective electron transfer was obtained between immobilized molecules and the electrodes. This novel application of N-phenylmaleimide diazonium may facilitate the development of bioelectronic devices including biofuel cells, biosensors, and DNA and protein microarrays.

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Citations

Apr 28, 2012·Inorganic Chemistry·Atiya T Overton, Ahmed A Mohamed
Sep 21, 2010·Journal of the American Chemical Society·Yann R LerouxPhilippe Hapiot
Apr 20, 2011·Chemical Society Reviews·Daniel Bélanger, Jean Pinson
Nov 22, 2008·Biosensors & Bioelectronics·Anil Kumar SarmaShelley D Minteer
Jan 8, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Charles EsnaultJean-François Pilard
Oct 17, 2014·Journal of Molecular Recognition : JMR·Marc HovestädtWalter F M Stöcklein
Jul 30, 2016·Bioelectrochemistry·Karen LevrieTim Stakenborg
Oct 23, 2013·Langmuir : the ACS Journal of Surfaces and Colloids·Mie LillethorupKim Daasbjerg
Jul 14, 2017·Chemical Communications : Chem Comm·Felix RösickeNorbert H Nickel
Sep 8, 2017·Sensors·José Juan-ColásThomas F Krauss
Apr 11, 2018·Chemistry : a European Journal·Nicholas D J YatesAlison Parkin
Jun 13, 2018·Annual Review of Analytical Chemistry·Elena E Ferapontova
Mar 9, 2021·ACS Applied Materials & Interfaces·Ting WuAlison J Downard
May 14, 2009·Langmuir : the ACS Journal of Surfaces and Colloids·Jason C HarperSusan M Brozik
Jul 23, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Ahmad A L AhmadAhmed A Mohamed
Dec 2, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·Mutsuo TanakaOsamu Niwa
Jan 8, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Al-Monsur Jiaul Haque, Kyuwon Kim
Nov 11, 2017·ACS Applied Materials & Interfaces·Ophélie SquillaceGuillaume Brotons
Sep 15, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Ting WuAlison J Downard
Oct 16, 2021·Analytical Methods : Advancing Methods and Applications·Cynthia P McCordCharles S Henry

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