Literature DB >> 20698664

High density orthogonal surface immobilization via photoactivated copper-free click chemistry.

Sara V Orski1, Andrei A Poloukhtine, Selvanathan Arumugam, Leidong Mao, Vladimir V Popik, Jason Locklin.   

Abstract

Surfaces containing reactive ester polymer brushes were functionalized with cyclopropenone-masked dibenzocyclooctynes for the light activated immobilization of azides using catalyst-free click chemistry. The photodecarbonylation reaction in the amorphous brush layer is first order for the first 45 s with a rate constant of 0.022 s(-1). The catalyst-free cycloaddition of surface bound dibeznocyclooctynes proceeds rapidly in the presence of azides under ambient conditions. Photolithography using a shadow mask was used to demonstrate patterning with multiple azide containing molecules. This surface immobilization strategy provides a general and facile platform for the generation of multicomponent surfaces with spatially resolved chemical functionality.

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Year:  2010        PMID: 20698664     DOI: 10.1021/ja105066t

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  21 in total

1.  Polar dibenzocyclooctynes for selective labeling of extracellular glycoconjugates of living cells.

Authors:  Frédéric Friscourt; Petr A Ledin; Ngalle Eric Mbua; Heather R Flanagan-Steet; Margreet A Wolfert; Richard Steet; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2012-03-09       Impact factor: 15.419

2.  Metal-free sequential [3 + 2]-dipolar cycloadditions using cyclooctynes and 1,3-dipoles of different reactivity.

Authors:  Brian C Sanders; Frédéric Friscourt; Petr A Ledin; Ngalle Eric Mbua; Selvanathan Arumugam; Jun Guo; Thomas J Boltje; Vladimir V Popik; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2010-12-23       Impact factor: 15.419

Review 3.  Achieving Controlled Biomolecule-Biomaterial Conjugation.

Authors:  Christopher D Spicer; E Thomas Pashuck; Molly M Stevens
Journal:  Chem Rev       Date:  2018-07-24       Impact factor: 60.622

4.  Strain-promoted alkyne-azide cycloadditions (SPAAC) reveal new features of glycoconjugate biosynthesis.

Authors:  Ngalle Eric Mbua; Jun Guo; Margreet A Wolfert; Richard Steet; Geert-Jan Boons
Journal:  Chembiochem       Date:  2011-06-09       Impact factor: 3.164

5.  Spatial and temporal control of the alkyne-azide cycloaddition by photoinitiated Cu(II) reduction.

Authors:  Brian J Adzima; Youhua Tao; Christopher J Kloxin; Cole A DeForest; Kristi S Anseth; Christopher N Bowman
Journal:  Nat Chem       Date:  2011-01-30       Impact factor: 24.427

6.  Facile Quenching and Spatial Patterning of Cylooctynes via Strain-Promoted Alkyne-Azide Cycloaddition of Inorganic Azides.

Authors:  Matthew Bjerknes; Hazel Cheng; Christopher D McNitt; Vladimir V Popik
Journal:  Bioconjug Chem       Date:  2017-05-09       Impact factor: 4.774

7.  Photocatalytic surface patterning of cellulose using diazonium salts and visible light.

Authors:  Peter Schroll; Charlie Fehl; Stephan Dankesreiter; Burkhard König
Journal:  Org Biomol Chem       Date:  2013-08-21       Impact factor: 3.876

8.  Post-assembly functionalization of organoplatinum(II) metallacycles via copper-free click chemistry.

Authors:  Rajesh Chakrabarty; Peter J Stang
Journal:  J Am Chem Soc       Date:  2012-08-28       Impact factor: 15.419

9.  Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) for metal-free click ligations.

Authors:  Christopher D McNitt; Vladimir V Popik
Journal:  Org Biomol Chem       Date:  2012-10-03       Impact factor: 3.876

10.  Multi-Functionalization of Polymers by Strain-Promoted Cycloadditions.

Authors:  Petr A Ledin; Nagesh Kolishetti; Geert-Jan Boons
Journal:  Macromolecules       Date:  2013-10-08       Impact factor: 5.985

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