Synthesis and ring-opening metathesis polymerisation of -alkoxy benzothiadiazole paracyclophane-1,9-dienes.

-Diethylhexyloxyphenylene benzothiadiazole paracyclophane-1,9-diene as a mixture of diastereomers was synthesized by a sequential benzyne-induced Stevens rearrangement, oxidation and pyrolysis of a dithia[3.3]paracyclophane. Reaction of these highly strained cyclophanedienes with the second generation Grubbs catalyst showed that they can be ring opened to alternating ,-phenylenevinylene polymers.

Synthesis and Ring-Opening Metathesis Polymerization of -Dialkoxy Paracyclophanedienes.

The highly strained -diethylhexyloxy [2.2]paracyclophane-1,9-diene () can be synthesized by ring contraction of a dithia[3.3]paracyclophane using a benzyne-induced Stevens rearrangement.

Modular synthesis of unsymmetrical [1]benzothieno[3,2-][1]benzothiophene molecular semiconductors for organic transistors.

A modular approach to underexplored, unsymmetrical [1]benzothieno[3,2-][1]benzothiophene (BTBT) scaffolds delivers a library of BTBT materials from readily available coupling partners by combining a transition-metal free Pummerer CH-CH-type cross-coupling and a Newman-Kwart reaction. This effective approach to unsymmetrical BTBT materials has allowed their properties to be studied. In particular, tuning the functional groups on the BTBT scaffold allows the solid-state assembly and molecular orbital energy levels to be modulated.