Assoc Prof. Wakamiya, A., Dr. Zhou, Z., et. al. ”Development of a New Method for the Boron-doping of Two Dimensional Carbon Materials” (Published in “Journal of the American Chemical Society” 28 February 2012)

Development of a New Method for the Boron-doping of Two Dimensional Carbon Materials

 

Published in “Journal of the American Chemical Society“(Online Publication, February 28, 2012).

 

Assoc Prof. Wakamiya, A., Dr. Zhou, Z., et. al.
(Structural Organic Chemistry, Division of Synthetic Chemistry )

Dr. Zhou, Z. and Assoc Prof.Wakamiya, A. (from left)
Assoc Prof. Atsushi Wakamiya, Dr. Zhiguo Zhou, Mr. Tomokatsu Kushida (Nagoya University), and Prof. Shigehiro Yamaguchi (Nagoya University) developed a new method for the boron-doping of two dimensional carbon materials, which is expected to be a promising approach towards the development of highly efficient electron transporting materials for organic electronics.

A crucial issue in the field of organic electronics is the development of efficient electron transporting materials. The recent development of hole-transporting materials in the field of in organic photovoltaics has resulted in an improvement of the light-to-electricity conversion efficiency to 10%, even though the electron-transporting materials have been limited almost to fullerene derivatives. The development of new electron-transporting materials is therefore a key step for the development of organic photovoltaic materials with significantly increased light-to-electricity conversion efficiencies. A promising molecular design approach for novel electron-transporting materials is the incorporation of boron atoms (boron-doping) into two dimensional carbon networks (Figure1). However, in order to successfully implement the concept of “boron-doping” into the development of these materials, the crucial problem of stabilizing the resulting boron-containing organic compounds has to be overcome.

Figure 1. Development of electron-transporing materials from two dimensional carbon networks by boron-doping.
The research group proposed a new concept for the kinetic stabilization of boron-containing materials based on “structural constraint”(Figure2). They have developed an effective synthetic method for the synthesis of model compounds and showed that a series of corresponding boron-containing carbon materials revealed high electron accepting abilities as well as high stability towards air and heat . These results demonstrate a new paradigm for the kinetic stabilization of boron-containing two dimensional carbon polycyclic skeletons in the absence of bulky aryl groups. T hese results should furthermore allow the development of a new class of fascinating 2D carbon materials with boron as the key element. The application of this method to boron-embedded graphene, low molecular weight polycyclic carbon materials, as well as fullerenes and carbon nanotubes would lead to the development of excellent electron-transporting materials that can realize higher light-to-electricity conversion efficiencies in organic photovoltaics.

Figure 2. Introducion of a new concept for the kineic stabilizaion of boron-containing materials based on “structural
constraint”.
Zhou, Z.; Wakamiya, A.; Kushida, T.; Yamaguchi. S., Planarized Triarylboranes: Stabilization by Structural Constraint and Their Plane-to-Bowl Conversion, J. Am. Chem. Soc., DOI:10.1021/ja211944q (2012).