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Probing the Versatility of Shape-Persistent Tetraphenylmethane Dendrimers by Modification of the Skeleton

preprint
submitted on 07.10.2019 and posted on 11.10.2019 by Julio Ignacio Urzúa, Sandra Campana, Massimo Lazzari, Mercedes Torneiro
Tetraphenylmethane has emerged as a recurrent building block for advanced porous materials such as COFs, PAFs and hypercrosslinked polymers. Guided by a similar design principle, we have previously synthesized shape-persistent dendrimers with tetraphenylmethane nodes and ethynylene linkers. Here we report the generality of our approach by describing new dendritic architectures built from tetraphenylmethane. First, we prepared expanded dendrimers where the tetrahedral units are bonded through larger rigid rod spacers. Among the different synthetic strategies tested, the convergent route, with alternating steps of Pd-catalyzed Sonogashira coupling and alkyne activation by removal of TMS masking groups, efficiently afforded the first- and second-generation dendrimers. A second type of compounds having a linear diyne at the core is also described. The dendrimers of generations 1-2 were also synthesized by a convergent approach, with the diyne being assembled in the last step of the synthesis by a Glaser oxidative homocoupling of the corresponding dendrons bearing a terminal alkyne at the focal point. A third-generation dendrimer was also successfully prepared by a double-phase strategy.

Funding

PGC2018-101047-B-I00

MAT2013-42425-R

History

Email Address of Submitting Author

mercedes.torneiro@usc.es

Institution

Universidade de Santiago de Compostela

Country

Spain

ORCID For Submitting Author

0000-0003-0914-1769

Declaration of Conflict of Interest

No conflict of interest

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