Doubly Cavitand-Capped Porphyrin Capsule by Hydrogen Bonds

The components of a 1:2 mixture of meso‐tetrakis(4‐dodecyl‐3,5‐dihydroxyphenyl)porphyrin (1) and a bowl‐shaped tetrakis(4‐pyridylethynyl)cavitand (2) in CDCl3 or C6D6 self‐assemble quantitatively into the doubly cavitand‐capped porphyrin capsule 2⋅1⋅2 through eight ArOH⋅⋅⋅Npy hydrogen bonds. Capsule 2⋅1⋅2 possesses two cavities divided by the porphyrin ring and encapsulates two molecules of 1‐acetoxy‐3,5‐dimethoxybenzene (G) as a guest to form G/G@(2⋅1⋅2). Remarkable solvent effect was observed, in which the apparent association constant of 2⋅1⋅2 with G in C6D6 was much greater than that in CDCl3. Porphyrin sandwich! A 1:2 mixture of resorcinol‐porphyrin 1 and pyridylethynyl cavitand 2 self‐assembles into doubly cavitand‐capped porphyrin capsule 2⋅1⋅2 through eight ArOH⋅⋅⋅Npy hydrogen bonds, which encapsulates two guest molecules (see figure).