Surface functionalization of 4-6nm nanodiamonds with conjugated aromatic ligands for application in organic electronics
Bruna Bregadiolli a b, Luiz Carlos Silva-Filho c, Maria Aparecida Zaghete a, Alan Sellinger b
a Institute of Chemistry, São Paulo State University (UNESP), Araraquara SP 14800-060, Brazil.
b Chemistry Department, Colorado School of Mines, Golden, Colorado 8040, USA.
c Chemistry Department, São Paulo State University (UNESP), Bauru, SP 17033-360 Brazil.
Proceedings of International Conference on Advances in Organic and Hybrid Electronic Materials (AOHM19)
Dubrovnik, Croatia, 2019 March 17th - 20th
Organizers: Alejandro Briseno, Thuc-Quyen Nguyen and Natalie Stingelin
Poster, Bruna Bregadiolli, 059
Publication date: 8th January 2019

Carbon allotropes have been an intensively investigated class of compounds. Among them, diamond nanoparticles (CND) recently have shown great potential for a variety of applications in medicine, sensing, catalytic areas and electronic devices.[1] CND are known as an interesting hybrid material consisting of the graphene-based shell with the intrinsic properties of a diamond core.[2-3] Considering these promising aspects, grafting conjugated ligands on the surface of CND to form functional materials that combine the properties from CND with the ligand is an interesting strategy to achieve novel optoelectronic materials.[4] We have developed a synthetic route to introduce aldehyde groups onto the CND sp2 shell by the Vilsmaier-Haack reaction. We then use both Knoevenagel and Horner-Wadsworth-Emmons chemistry to attach either electron withdrawing or donating ligands onto the CND surface. Octyl-cyanoacetate was selected in order to: improve solubility of the material, test for electron withdrawing properties and thin film deposition. The new material synthesized was structurally (FT-IR, NMR and Raman spectroscopies), optically (UV-vis), and electrochemically (CV) characterized. In addition to the good solubility and intrinsic electronic features for the ligand, the π–π interaction between the anchoring groups and the CND spshell can tailor the band gap of the composite. Consequently, grafting ligands onto the CND surface may form advanced functional materials that could be applied in various electronic devices.

The authors would like to thank São Paulo Research Foundation (FAPESP 2017/07627-0 and2018/02084-0) for financial support.

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