Oral Presentation Royal Australian Chemical Institute National Congress 2026

Synthesis of Novel Antipodally Substituted closo Carboranes (136742)

Thomas J.C. Carraro 1 , Eliash M. Hemzal 1 , Lou M. Rendina 1
  1. The University of Sydney, Camperdown, NSW, Australia

Closo-1,12-carborane (para-carborane) is one of the few molecular building blocks capable of forming straight, rigid molecular rods, making it valuable in nanoscience, medicinal chemistry, and materials science. The main use of para-carborane are the two readily functionalised C-H vertices, antipodal to each other on the icosahedral cage. In addition to its favourable geometry, the carborane cage is an excellent electrical insulator and exhibits exceptional resistance to thermal, X-ray, and UV-induced degradation. Consequently, closo-1,12-carborane has been widely employed in rigid-rod nanoarchitectures, molecular rotors and nanomachines, liquid crystals, non-linear optical materials, metal–organic framework spacers, and in medical applications including boron neutron capture therapy and anti-androgen design.

Despite these advantages, broader implementcation of the 1,12-closo-carborane framework remains limited by poor commercial availability due to it synthetically demanding, low-yielding preparation. Herein, we report the synthesis of a novel antipodal dihalogenated carborane derived from the more readily accessible 1,7-closo-carborane. This compound represents a viable isostructural alternative to 1,12-closo-carborane and offers a practical route to rigid, linear carborane-based architectures for future applications across materials science and chemical biology.