In recent years, end-functional poly(3-hexylthiophene) (P3HT) has proven to be instrumental in the continued development and innovation within the broad conjugated polymer arena, enabling a variety of applications, particularly in organic electronics. The availability of P3HT with controlled molecular weights, low polydispersity, and importantly, a wide range of reactive end-groups not only serves as a key building block for the preparation of conjugated block copolymers but also facilitates the development of hybrid nanocomposite materials via inorganic surface modification strategies. This Highlight focuses on the synthetic approaches to endfunctional P3HT and the impact of these systems in emerging technologies. V C 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 831-841
We have developed an efficient synthetic platform for the preparation of a new class of high performance thermosets based on the 1,3-dipolar cycloaddition of a bifunctional sydnone with a trifunctional alkyne. These processable materials possess outstanding thermal stability, with Td5% of 520 °C and a weight loss of <0.1% per day at 225 °C (both in air). Key to this performance is the stability of the starting functional groups that allows for reactive B-staging via simple thermal activation to give fully aromatic and highly cross-linked polypyrazole-based thermosets.
Via Sonogashira cross-coupling with different alkynes, 1,6 and 1,7 perylene diimides (PDIs) and perylene tetracarboxylic dianhydrides (PTCDs) were synthesized from the corresponding regioisomeric mixture of 1,6/1,7-dibromo precursors. Both bulky triphenyl propyne (TPP) groups and nonbulky hexyl groups allow for facile chromatographic separation. The optical properties of these compounds are discussed. Neutral bay substituents hypsochromically shift both the absorption and emission through deformation from planarity of the perylene core.
Modular synthesis of asymmetric rylenes from commercially available naphthalic anhydride derivatives provides access to novel materials with tunable functional handles at the imide-position, site-specific incorporation of bay position substituents and tailored extension of the molecular core.
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