title: Synthesis and Atropisomerism of Cascaded Tetraphenylporphyrin-[60]Fullerene Hybrids.
abstract: Flexible, linked dendritic tetraphenylporphyrin (TPP)-fullerene hybrids were synthesized. They were designed to gain insight into and mimic the primary events in the natural photosynthetic reaction center. These multiporphyrin moieties are based on a light-harvesting concept. Moreover, they incorporate multiple redox components aligned along a redox gradient. Newkome-type dendrons were added to these TPP-fullerene hybrids. In principle they can mediate pH-dependent water solubility, which, however, could not be observed in this case. A protecting-group strategy using tert-butyldiphenylsilyl groups allows convergent synthesis of the dendritic compounds. The dendritic multiporphyrins were synthesized separately and can be used as individual building blocks. Atropisomerism was observed in the dendritic compounds, and single atropisomers could be assigned to the corresponding peaks of a characteristic pattern in the NMR spectra. Deprotection of the Newkome-type dendrons was shown to be feasible under mild conditions that leave the redox gradient intact.
authors.affiliation: Department of Chemistry and Pharmacy & Interdisciplinary Center of Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany), Fax: (+49) 9131-852-6864.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Schlundt
authors.affiliation: Department of Chemistry and Pharmacy & Interdisciplinary Center of Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany), Fax: (+49) 9131-852-6864.
authors.forename: Walter
authors.initials: W
authors.lastname: Bauer
authors.affiliation: Department of Chemistry and Pharmacy & Interdisciplinary Center of Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany), Fax: (+49) 9131-852-6864. andreas.hirsch@fau.de.
authors.forename: Andreas
authors.initials: A
authors.lastname: Hirsch
mesh_terms: D050091:Dendrimers / Q000138:chemical synthesis* / Q000737:chemistry; D037741:Fullerenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D012833:Siloxanes / Q000737:chemistry*; D012995:Solubility
chemical_list: D050091:Dendrimers; D037741:Fullerenes; D011166:Porphyrins; D012833:Siloxanes; C409084:tetraphenylporphyrin
keywords: atropisomerism; dendrons; fullerenes; metallocenes; porphyrinoids