Stable soluble conjugated carbon rods with a polytriacetylene backbone

2 Stable Soluble Conjugated Carbon Rods with a Polytriacetylene Backbone 

Modem acetylene chemistry plays a critical role in the current world-wide efforts to synthesize new molecular and polymeric carbon allotropes as well as carbon-rich nanomaterials. It is rapidly becoming clear that the preparative challenges in this interdisciplinary research area at the interface between materials science and chemistry are formidable and rival those in the more established synthesis of natural products and biologically active compounds. Modern materials research strongly relies on advanced synthetic methodology, and it is hoped that the field will attract many synthetically oriented chemists into its ranks their efforts will be rewarded by the development of materials with unique properties and unprecedented applications. 

To a solution of 29 (1.0 g, 1.3 mmol) in dry THF (10 mL) at -78°C was added slowly a solution of LDA in THF [10 mL, 7.8 mmol prepared by the addition of 4.9 mL of -BuLi (1.6 M in hexane) to a solution of diisopropylamine (0.8 g) in THF (10 mL) at 0°C]. The solution turned bright green, then blue, and finally purple, signifying the complete reaction of the tetrabromide. After 10 min, saturated aqueous NH4CI (5 mL) was added, and the solution rapidly turned pale yellow. The THF solution was diluted with hexane and extracted with H2O (2 X). The hexane layer was filtered through a plug of silica gel and concentrated to 5 mL. After 12 h at -20°C, crystals had formed which were filtered to give 30 a (0.54 g, 95%) mp 76 °C (dec.). 

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