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. 2015 Dec;19(12):1256-1261.
doi: 10.1142/S1088424615501084.

Solid-state Porphyrin Interactions with Oppositely Charged Peripheral Groups

W Robert Scheidt  1 , Beisong Cheng  1 , Allen G Oliver  1 , John A Goodwin  2
Affiliations

Solid-state Porphyrin Interactions with Oppositely Charged Peripheral Groups

W Robert Scheidt et al. J Porphyr Phthalocyanines. 2015 Dec.

Abstract

The crystallization and the crystal and molecular structure of a very slightly soluble electrostatically interacting pair of porphyrins is described. The tetra-anion 5,10,15,20-tetrakis-(4-sulfonatophenyl)-21,23H-porphyrin [H2TPPSO3]4- and the tetra-cation 5,10,15,20-tetra(N-methylpyridyl)21H,23H-porphyrin [H2TMePyP]4+ are found to form an alternating one-dimensional stack that is stabilised by electrostatic interactions between the porphyrin rings but also by π-π interactions between all substituted phenyl rings in the ensemble. The resulting interactions between the porphyrins is exceptionally tight.

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Figures

Figure 1
Figure 1
Illustrations of [H2TMePyP]4+ and [H2TPPSO3]4−.
Figure 2
Figure 2
Schematic illustration of the U-tube assembly used to prepare crystals of [H2TMePyP–H2TPPSO3]·5H2O. The diameter of the tube is 1 cm.
Figure 3
Figure 3
Formal diagram of the porphyrin cores in (a) the [H2TMePyP]4+ cation and (b) the [H2TPPSO3]4− anion showing the averaged values of the unique classes of bond distances and angles in the 24-atom porphyrin cores. Values of the perpendicular displacement, in units of 0.01 Å, of each atom from the mean plane of the 24-atomn core is given.
Figure 4
Figure 4
ORTEP drawing (parallel projection) of four porphyrin rings in the stack of the electrostatically interacting [H2TMePyP–H2TPPSO3]·5H2O system. The center···center distance of 4.253 Å, the lateral shift of 1.88 Å, the slip angle of 26.4°, and the mean plane separation of 3.81 Å are applicable to any adjacent pair of porphyrin rings. Thermal ellipsoids are drawn at the 5% level.
Figure 5
Figure 5
ORTEP drawing of [H2TMePyP–H2TPPSO3]·5H2O illustrating the cofacial interaction between the peripherally charged cationic (heavy bonds) and anionic (lighter) rings. (parallel projection, 40% probability surfaces).
Figure 6
Figure 6
ORTEP drawing of [H2TMePyP–H2TPPSO3]·5H2O illustrating the cofacial interaction between the peripherally charged cationic (heavy bonds) and anionic (lighter) rings. (parallel projection, 40% probability surfaces).
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