Abstract
The preparation of the shape-persistent carbosilane-functionalized porphyrins H2TPP(4-SiRR'Me)4, Zn(II)-TPP(4-SiRR'Me)4 (R = R' = Me, CH2CH=CH2, CH2CH2CH2OH; R = Me, R' = CH2CH=CH2, CH2CH2CH2OH; TPP = tetraphenyl porphyrin), H2TPP(4-Si(C6H4-1,4-SiRR'Me)3)4, and Zn(II)-TPP(4-Si(C6H4-1,4-SiRR'Me)3)4 (R = R' = Me, CH2CH=CH2; R = Me, R' = CH2CH[double bond, length as m-dash]CH2) using the Lindsey condensation methodology is described. For a series of five samples their structures in the solid state were determined by single crystal X-ray structure analysis. The appropriate 0th and 1st generation porphyrin-based 1,4-phenylene carbosilanes form 2D and 3D supramolecular network structures, primarily controlled by either π-π interactions (between pyrrole units and neighboring phenylene rings) or directional molecular hydrogen recognition and zinc-oxygen bond formation in the appropriate hydroxyl-functionalized molecules. UV-Vis spectroscopic studies were carried out in order to analyze the effect of the dendritic branches on the optical properties of the porphyrin ring.
Highlights
Branched macromolecular architectures as well as selfassembly processes have become very popular and represent fascinating research areas both in natural sciences and engineering.[1]
For the preparation of the carbosilane dendrimer-based porphyrins 3a–c (Scheme 1) the synthetic methodology developed by Lindsey was used.[20]
The structures of five samples (3b,c, 4a, 6a, 9b) in the solid state have been determined by single X-ray structure determination
Summary
Branched macromolecular architectures as well as selfassembly processes have become very popular and represent fascinating research areas both in natural sciences and engineering.[1]. The 2D layers are formed along the crystallographic a- and b-axes, but not along the crystallographic c-axes as depicted in Fig. S1 and S2.† only the C6H4 aromatic group comprising the atoms C11 to C16 and symmetry generated analogues is involved in T-shaped π–π interactions with the C20N4 core of adjacent molecules.
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