Synthesis of Molecular Tripods Based on a Rigid 9,9'-Spirobifluorene Scaffold

Valášek, Michal and Edelmann, Kevin and Gerhard, Lukas and Fuhr, Olaf and Lukas, Maya and Mayor, Marcel. (2014) Synthesis of Molecular Tripods Based on a Rigid 9,9'-Spirobifluorene Scaffold. Journal of Organic Chemistry, 79 (16). pp. 7342-7357.

Full text not available from this repository.

Official URL: http://edoc.unibas.ch/dok/A6337622

Downloads: Statistics Overview


The efficient synthesis of a new tripodal platform based on a rigid 9,9′-spirobifluorene with three acetyl protected thiol groups in the positions 2, 3′ and 6′ for deposition on Au(111) surfaces is reported. The modular 9,9′-spirobifluorene platform provides both a vertical arrangement of the molecular rod in position 7 and its electronic coupling to the gold substrate. To demonstrate the validity of the molecular design, the model compound 24 exposing a para-cyanophenylethynyl rod is synthesized. Our synthetic approach is based on a metal–halogen exchange reaction of 2-iodobiphenyl derivative and his subsequent reaction with 2,7-disubstituted fluoren-9-one to afford the carbinol 16. Further electrophilic cyclization and separation of regioisomers provided the corresponding 2,7,3′,6′-tetrasubstituted 9,9′-spirobifluorene 17 as the key intermediate. The molecular structure of 17 was determined by single-crystal X-ray diffraction crystallography. The self-assembly features of the target compound 24 were analyzed in preliminary UHV-STM experiments. These results already demonstrated the promising potential of the concept of the tripodal structure to stabilize the molecule on a Au(111) surface in order to control the spatial arrangement of the molecular rod.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Molecular Devices and Materials (Mayor)
UniBasel Contributors:Mayor, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:05 Apr 2017 09:58
Deposited On:06 Feb 2015 09:59

Repository Staff Only: item control page