Communication
Macromolecular
Rapid Communications
wileyonlinelibrary.com 1486 © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim DOI: 10.1002/marc.201500184
1. Introduction
Nature fascinates researchers by its remarkable mate-
rials: gecko feet, lotus leaves, spider silk, butterfly wings
are just a few examples for scientific inspiration. These
materials possess interesting and unique properties,
The functionalization of zinc oxide (ZnO) nanoparticles by poly(3-hexylthiophene) (P3HT)
brush is completed by the combination of a mussel inspired biomimetic anchoring group and
Huisgen cyclo-addition “click chemistry.” Herein, the direct coupling of an azide modified cat-
echol derivative with an alkyne end-functionalized P3HT is described. This macromolecular
binding agent is used to access core@corona ZnO@P3HT with a stable and homogeneous con-
jugated organic corona. Preliminary photoluminescence
measurement proves an efficient electron transfer from
the donor P3HT to the acceptor ZnO nanoparticles upon
grafting, thus demonstrating the potential of such a com-
bination in organic electronics.
Biomimetic Mussel Adhesive Inspired Anchor
to Design ZnO@Poly(3-Hexylthiophene) Hybrid
Core@Corona Nanoparticles
Hussein Awada, Leila Mezzasalma, Sylvie Blanc, Delphine Flahaut,
Christine Dagron-Lartigau, Joël Lyskawa, Patrice Woisel,
Antoine Bousquet,* Laurent Billon*
Dr. H. Awada, L. Mezzasalma, Dr. C. Dagron-Lartigau,
Dr. A. Bousquet, Prof. L. Billon
IPREM CNRS-UMR 5254
Université de Pau et des Pays de l’Adour
Equipe de Physique et Chimie des Polymere
Hélioparc 2 avenue Président Angot
64053, Pau Cedex 9, France
E-mail: antoine.bousquet@univ-pau.fr;
laurent.billon@univ-pau.fr
Dr. S. Blanc, Dr. D. Flahaut
IPREM CNRS-UMR 5254 , Université de Pau et des Pays de
l’Adour, Equipe de Chimie Physique, Hélioparc, 2 avenue
Président Angot 64053, Pau Cedex 9, France
Dr. J. Lyskawa, Prof. P. Woisel
Unité Matériaux et Transformations CNRS UMR 8207 –
Université de Lille 1, ENSCL, Bât. C6 59655
Villeneuve d’Ascq, France
which drive the development of new smart and respon-
sive synthetic materials. Mussels are adapted to survive in
tidal zones where they strongly attach to many substrates
such as rocks, wooden piers, metal bridges, or ships. In
1981, catechols have been identified by Waite and Tanzer
to be the main functionality responsible for the versa-
tile adhesion of mussels in the most inhospitable regions
(under very harsh and wet conditions).
[1]
This amazing
behavior inspired scientist to functionalize different sub-
strates using catechols or 3,4-dihydroxyphenyl-l-alanine.
[2]
Specific adhesion mechanisms of these molecules to sur-
faces are still not completely understood but seem to be
substrate dependent.
[3]
However, in all cases, covalent or
strong noncovalent interactions can be found between
catechol groups and inorganic substrates.
[4]
As far as metal
oxides are concerned, catechol groups are assumed to form
bidentate bonding with the surfaces.
[5]
Polymer chemists have recently started to use cat-
echol to graft different kinds of macromolecules such as
polypeptides,
[6]
glycopolymers,
[7]
poly(ethylene glycol),
[8]
or polynorbornene derivative made via ROMP.
[9]
Con-
trolled radical polymerization has also been combined
with catechol to surface initiate the oligo ethylene glycol
Macromol. Rapid Commun. 2015, 36, 1486−1491