The innovation engine for new materials

Calvin Lin

Calvin Lin


University of California, Santa Barbara



Faculty Sponsor(s): 

Luis Echegoyan

Faculty Sponsor's Department(s): 

Chemistry and Biochemistry

Project Title: 

Design and synthesis of tetrakis and hexakis-fullerene linkers for the construction of 2D and 3D extended framework structures

Project Description: 

Metal-organic frameworks (MOFs), consisting of metal ions coordinated with organic ligands, are a relatively new and emerging class of materials. MOFs have been shown to be promising candidates for numerous chemical and practical applications such as gas storage, catalysis, and sensors. Although structures of one-dimensional1 and two-dimensional metal-organic coordination polymers2 have been obtained by our group, fullerenes have yet to be incorporated into three-dimensional metal-organic structures. Recently, a linear polymer was prepared by complexing a fullerene derivative possessing four malonates in an equatorial belt and two 4,5-diazafluorene (DAF) groups located at trans-1 positions, with Cu2+. The present work attempts to further this concept into two and three axes of propagation in order to develop two-dimensional and three-dimensional MOFs, respectively. Herein, we report the synthesis of a novel fullerene derivative which has great potential in coordinating with metals to form 2D MOFs. Based on the encouraging results of a linear polymeric structure, we designed the synthesis of a tetrakis-4,5-diazafluorene fullerene derivative which can be further converted to a hexa-DAF fullerene derivative. We started from a trans-1 C60 bis-anthracene derivative which possesses four reactive bonds in an equatorial belt for further functionalization. By reaction with DAF under room temperature conditions, we achieved the synthesis of the tetrakis-DAF derivative in an acceptable yield. We plan to achieve the two-dimensional MOF and three-dimensional MOF by linking equatorial tetra-DAF fullerene derivatives and hexa-DAF fullerene derivatives with metal ions. Both fullerene derivatives were synthesized using the Kräutler and Bingel-Hirsch reactions.