Use of Unprecedented Intramolecular 1, 3-Dipolar Cycloaddition Reaction in meso-Nitrile Oxide-Containing BODIPYs as a New Pathway for the Preparation of Fused NIR Platforms.

Meso-nitrile oxide group in 1,7-Diphenyl-containing BODIPYs can be involved in highly unusual [3+2] intramolecular cycloaddition reaction with the formation of the dihydrobenzo[d]isoxazole-containing BODIPYs. Oxidation of these compounds results in the formation of unprecedented either benzisoxazole- or benzo[b]azepine-fused fully conjugated NIR absorbing BODIPYs. The photophysical properties and electronic structures of the target compounds were studied by an array of experimental and theoretical methods.

A Laboratory Preparation of High-Purity Calcium Cyanamide.

Calcium cyanamide is an important fertilizer and a chemical precursor. However, its large scale synthesis is extremely energy intensive via the historical Frank-Caro synthesis of fixing atmospheric nitrogen with calcium carbide at an elevated temperature, and the product material contains a large number of impurities. In this work, we prepare calcium cyanamide in a purity higher than that achievable by the Frank-Caro route in a convenient laboratory method.