A Nanotube of Cyclic Porphyrin Dimers Connected by Nonclassical Hydrogen Bonds and Its Inclusion of C₆₀ in a Linear Arrangement

Abstract

Wie Erbsen in einer Schote sind einer Röntgenstrukturanalyse zufolge die C60‐Moleküle in einem supramolekularen Einschlusskomplex mit cyclischen Porphyrindimeren aufgereiht (siehe Bild; N blau, Ni grün). Die cyclischen Moleküle stapeln sich durch nichtklassische C‐H⋅⋅⋅N‐Wasserstoffbrücken und π‐π‐Wechselwirkungen zwischen Pyridylgruppen zu einer Röhrenstruktur, die C60‐Moleküle in linearer Anordnung aufnehmen kann.

Supramolecular Structures and Photoelectronic Properties of the Inclusion Complex of a Cyclic Free‐Base Porphyrin Dimer and C60

“…[26] On the basis of the titration of H 4 -CPD Py with C 60 , the association constant (K assoc ) was determined to be 9.6 10 4 m À1 ( Figure S3 in the Supporting Information). [26] This value is nearly half that of Ni 2 -CPD Py [18] and is smaller than that of the cyclic free-base porphyrin dimer (7.5 10 5 m…”

“…These interactions are similar to those of the crystal structure of Ni 2 -CPD Py . [18] The center-to-center distance between porphyrins along this tubular assembly is 14.895 for H 4 -CPD Py . In both Ni 2 -CPD Py and H 4 -CPD Py , each tube axis is not parallel with the vector joining the pyridyl-substituted meso carbon atoms; that is, each vector has a certain oblique angle to each tube axis.…”

“…[18] In this complex (C 60 &Ni 2 -CPD Py ), C 60 molecules are linearly arranged in the inner channel of the porphyrin nanotube to form a supramolecular peapod. In addition, the complex exhibits a high anisotropic electron mobility (Sm = 0.72 cm 2 V À1 s…”

Silver‐Mediated Formation of a Cofacial Porphyrin Dimer with the Ability to Intercalate Aromatic Molecules

“…

Porphyrins are widely used for functional molecular systems based on their excellent photophysical and redox properties. [2,3] Cofacial porphyrin dimers can be readily constructed by linking two porphyrin rings by covalent, [4][5][6][7][8][9][10][11][12] hydrogen, [13] or coordination bonds. [2,3] Cofacial porphyrin dimers can be readily constructed by linking two porphyrin rings by covalent, [4][5][6][7][8][9][10][11][12] hydrogen, [13] or coordination bonds.

…”

“…[2,3] Cofacial porphyrin dimers can be readily constructed by linking two porphyrin rings by covalent, [4][5][6][7][8][9][10][11][12] hydrogen, [13] or coordination bonds. For example, a fullerene molecule is captured by p-p interactions, [6,9,15] or various ligand molecules bind to the axial site of the central metals from inside. For example, a fullerene molecule is captured by p-p interactions, [6,9,15] or various ligand molecules bind to the axial site of the central metals from inside.…”