Toward nanotubes with periodic gaps: Carbon nanotubes consist of a continuous array of benzene rings fused along their edges. It is not straightforward to excise regular fragments in a top-down fashion to produce periodic gaps. Sun et al. showcase the beginnings of a bottom-up strategy toward this end. They used borylations and catalytic cross-coupling chemistry to prepare a discrete cylindrical carbon compound composed of 40 benzene rings bonded to one another at the 1, 3, and 5 positions to leave regular void spaces in the walls. Catenation of multiple similar segments could ultimately lead to an extended nanotube with periodic wall defects. Science , this issue p. 151
29 September 2014 in The Journal of Organic Chemistry
A modern electrophosphorescent organic light-emitting device (OLED) achieves quantitative electro-optical conversion by using multiple layers of molecular materials designed through role allotment for independent and specific functions. A unique, potentially innovative device architecture, i.e., a single-layer phosphorescent OLED, is currently being developed by designing multirole base materials via a structural combination of multiple functional components in single molecules. The multirole molecules, however, inevitably require multiple processes to synthesize their multiple components and, moreover, to assemble these components synthetically into one molecule. We herein show that the multirole base material for a highly efficient single-layer phosphorescent OLED can be designed and synthesized with a single, very simple aromatic hydrocarbon component of toluene merely through a one-pot macrocyclization. Without requiring the assembly tasks at the synthesis stage, the molecular design allows for a concise one-pot synthesis of, and a quantitative electro-optical conversion in, the single-layer device architecture with a single-component base material.
5 May 2014 in Journal of the American Chemical Society
Nitrogen-doped carbon nanotubes have attracted attention in various fields, but lack of congeners with discrete molecular structures has hampered developments based on in-depth, chemical understandings. In this study, a nanotube molecule doped periodically with multiple nitrogen atoms has been synthesized by combining eight 2,4,6-trisubstituted pyridine units with thirty-two 1,3,5-trisubstituted benzene units. A synthetic strategy involving geodesic phenine frameworks is sufficiently versatile to tolerate pyridine units without requiring synthetic detours. Crystallographic analyses adopting aspherical multipole atom models reveal the presence of axially rotated structures as a minor disordered structure, which also provides detailed molecular and electronic structures. The nitrogen atoms on the nanotube serve as chemically distinct sites covered with negatively charged surfaces, and they increase the chance of electron injections by lowering the energy levels of the unoccupied orbitals that should serve as electron acceptors.