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Theses Year : 2021

Synthesis of novel π-conjugated functional organic semiconductors for optoelectronic applications

Synthèse de nouveaux semi-conducteurs organiques fonctionnels conjugués π pour des applications optoélectroniques


Organic electronic devices have gained immense popularity in the last three decades because there are promising in terms of their tunable electronic properties, cost effectiveness, versatile functionalization, and processability. The key component of these devices is the organic semiconductor material, which acts as an active layer and determines the device performance. Discovering of novel high-performance building blocks and extending the library of organic semiconductors is one driving force in this filed. In this thesis, a series of novel π-conjugated materials were synthesized as n-type organic semiconductors and characterized by 1H NMR, 13C NMR spectroscopy, high resolution mass spectrometry, electrochemistry and UV-Vis spectroscopy. The manuscript consists of five chapters, and details of each chapter are as follows. Chapter 1 is a general introduction to organic semiconductors. Chapter 2 aims to further advances in the synthesis of organic semiconductors through a study of structure-property-morphology relationships in cross-conjugated 7,7’ disubstituted isoindigo materials. Oxindole is a key building block for the construction of isoindigo and chapter 3 explores the potential use of oxindole as a building block for the preparation of new A-D-A architecture based on π-conjugated bridge, with different bridge lengths. Our objective was to vary the conjugation length by different spacer groups and to alter the linkage position of the isatylidene malononitrile group (4 position vs. 6 position), to analyze the effect on its structural, photophysical and electrochemical properties. Chapter 4 aims to extend π-conjugation length of the isoindigo core, rather than its core-modification. This research is inspired by the renewed interest in the indophenine chemistry and targets to address the regioisomer issue. To this end we replaced the central double bond of isoindigo with quinoidal molecules based on EDOT units. These π-bridges are particularly suited since their provide π-spacer bridge together with good ability to act as conformational locking units to drive the formation of single isomer. In particular, in this chapter we describe the organic synthesis routes, the mechanisms of synthesis of products, physical characterization, UV-visible, electrochemistry, the structure property relationships within these molecules. With the help of 1H NMR experiments , 1H–1H COSY and 1H-1H NOESY analyses we showed a single isomer formation of these molecules. Last chapter demonstrates the fabrication of bio-interface for sensing. In fact, mixed ion/electron semiconducting polymers have recently emerged as promising materials for transducing signals at the interface between the biological elements and electronic devices. In this chapter we describe a study on a new bio-interface based on amphiphilic poly(3-hexylthiophene)-b-poly(3-triethylene-glycol-thiophene), for label-free impedimetric detection of Escherichia coli (E. coli). A set of amphiphilic conjugated random and block polythiophene that contain tetraethylene glycol side chains and possess mixed ionic and electronic conductivities have been synthesized, characterized and assessed as a bacteria biosensing material.
L'électronique organique est un domaine en plein essor, à l’interface de l’électronique, de la physique de la matière condensée, de la physico-chimie, et de la chimie organique. La découverte et le développement de nouveaux semi-conducteurs organiques ouvrent de nouvelles perspectives tant en sciences fondamentales qu’en termes d’applications. Ce travail décrit le développement de nouvelles voies de fonctionnalisation des systèmes p-conjugués en vue leurs applications potentielles comme semi-conducteur de type N. Le manuscrit est structuré en cinq chapitres, le premier fait un état de l'art récent sur la synthèse des semi-conducteurs organiques de type N. Le second chapitre décrit la synthèse et l'étude physico-chimique de quelques dérivés 7,7' isoindigo. Le troisième et le quatrième chapitre de ce travail décrit la synthèse d'une série de molécules A-D-A en modifiant les conditions classiques de la synthèse de l’indophénine et la mise au point de deux nouvelles voies de fonctionnalisation des dérivés de l’indophénine. Des études spectroscopiques et électrochimiques ont pu être menées, notamment afin de déterminer les énergies des orbitales frontières de nos molécules. Enfin, en dernier chapitre une étude exploratoire sur les propriétés de détection sélective de différents bactérie avec des polymères conjugués à conduction mixte a été entreprise.
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tel-03934578 , version 1 (11-01-2023)


  • HAL Id : tel-03934578 , version 1


Shiwei Ren. Synthesis of novel π-conjugated functional organic semiconductors for optoelectronic applications. Organic chemistry. Institut Polytechnique de Paris, 2021. English. ⟨NNT : 2021IPPAX044⟩. ⟨tel-03934578⟩
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