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- W2321492564 abstract "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." @default.
- W2321492564 created "2016-06-24" @default.
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- W2321492564 date "2014-07-25" @default.
- W2321492564 modified "2023-09-27" @default.
- W2321492564 title "Synthesis of Molecular Tripods Based on a Rigid 9,9′-Spirobifluorene Scaffold" @default.
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- W2321492564 doi "https://doi.org/10.1021/jo501029t" @default.
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