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Synthesis and self-assembly of triarylamines modified with nucleobases

Abstract : Triarylamines are small molecules widely used as charge carriers in the field of organic electronics as they display high hole-transport mobilities. In 2010, our group demonstrated for the first time that chemically-tailored triarylamine amide molecules undergo supramolecular polymerization. On the other hand, the recognition properties of nucleobase residues have been widely used in the last 25 years to trigger self-assembling processes of polymers or small molecules into well-defined supramolecular polymers.In this thesis, a series of triarylamine amide molecules decorated on their side chains with various nucleobases such as guanine, thymine and cytosine have been synthesized. We have demonstrated that the triarylamine monomers retain their self-assembling properties in chlorinated solvent upon light irradiation, provided that the nucleobase residue does not affect the non-covalent interactions necessary for the self-assembly of the triarylamine core. In addition, we have demonstrated that the presence of primary amines on the nucleobase residue prohibit the formation of self-assembled structures, as soon as they are not embedded in hydrogen bonding arrays. In a second chapter, the templated self-assemblies of our triarylamine-nucleobase molecules in organic solvents were studied. Firstly, templated supramolecular polymerization of triarylamine-monothymine using melamine in various solvents was investigated. Besides, selective influence of mercury ion on the light responsive properties of triarylamine-monothymine was analyzed carefully. At last, hybrid supramolecular polymers of triarylamine-monoguanine conjugate in absence and in presence of potassium ion were obtained. In particular, we have described the first example of supramolecular polymers build from melamine in organic solvents. Overall, the impact of this work is three-fold: a) it leads to a better understanding of the self-assembly behavior of triarylamine conjugates, b) it influences the design of self-assembling triarylamine structures and c) it offers new approaches for the self-assembly of triarylamine molecules.
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  • HAL Id : tel-02003342, version 1

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Qing Cao. Synthesis and self-assembly of triarylamines modified with nucleobases. Other. Université de Strasbourg, 2017. English. ⟨NNT : 2017STRAF001⟩. ⟨tel-02003342⟩

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