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A conjugated alternating copolymer containing norbornadiene and bis(ethynylene)phenylene units was prepared by the Cassar-Heck-Sonogashira cross-coupling reaction. Its electroluminescence was tested in a device, and its fluorescence colour could be tuned by light-induced norbornadiene-quadricyclane isomerization.

The continuous increase in the global energy demand deeply impacts the environment. Consequently, the research is moving towards more sustainable forms of energy production, storage and saving. Suitable technologies and materials are fundamental to win the challenge towards a greener and more eco-friendly society. Organic π-conjugated materials, including small molecules, oligomers and polymers are a wide and versatile class of functional materials with great potentiality, as they can be used as active matrixes in the fabrication of lightweight, flexible, cheap and large area devices. Their chemical and physical properties, both at a molecular level and mainly in the solid state, are a result of many factors, strictly related to the conjugated structure and functional groups on the backbone, which control the intermolecular forces driving solid state aggregations. The synthesis, through the molecular design, the choice of conjugated backbone and functionalization, represents the first and most powerful tool for finely tuning the chemico-physical properties of organic materials tailored for specific applications. In the present review, we report an overview of our works focused on synthetic methodologies, characterization, structure-properties correlation studies and applications of organic materials designed for energy-involving solid-state applications, organic photovoltaics in particular. The impact of functionalization on electro-optical properties and performance in device are discussed, also in relation to the specific applications. [ABSTRACT FROM AUTHOR]

Abstract: Poly(2′,5′-dioctyloxy-4,4′,4″-terphenylenevinylene) with (E) configuration of the vinylene double bonds was prepared by Suzuki–Miyaura polymerization of (E)-4,4′-dibromostilbene and 2,5-dioctyloxy-1,4-benzenediboronic acid. Attempts to extend this simple procedure to the synthesis of the polymer with (Z) configuration, starting from (Z)-4,4′-dibromostilbene, were unsuccessful. However, the use of (Z)-4,4′-diiodostilbene and a careful choice of Pd catalyst and experimental conditions, lead to a material with a >95/<5 (Z)/(E) ratio of vinylene units. The investigation of optical properties of both the (E) and (Z) polymers evidenced that (Z) linkages act as defects which reduce the effective conjugation length in the polymer backbone. [Copyright &y& Elsevier]