Nanographene-Fused Expanded Carbaporphyrin Tweezers

• DOI: 10.1021/jacs.3c10122
• Publication Date: 2023-12-26T19:13:50Z
• Authors: Haodan He; Yu Jin Lee; Zhaohui Zong; Ningchao Liu; Vincent M. Lynch; Jinseok Kim; Juwon Oh; Dongho Kim; Jonathan L. Sessler; Xian-Sheng Ke
• Keywords: Molecular tweezers; Dihedral angle; Tweezers

A nanographene-fused expanded carbaporphyrin (5) and its BF2 complex (6) were synthesized. Single-crystal X-ray structures revealed that 5 6 are connected by two hexa-peri-hexabenzocoronene (HBC) units dipyrromethene or BODIPY units, respectively. As prepared, both show nonaromatic character with figure-of-eight carbaoctaphyrin (1.1.1.0.1.1.1.0) cores adopt tweezers-like conformations characterized a partially confined space between the constituent HBC units. The distance centers is >10 Å, while dihedral angles planes 30.5 35.2° for 6, interactions fullerene C60 studied in organic media solid state. Proton NMR spectral titrations of 1:1 binding mode macrocycles. In toluene-d8, corresponding constants determined to be 1141 ± 17 994 10 M–1 diffraction structural analyses confirmed formation inclusion complexes guests found within triangular pockets composed from receptor most closely associated bound fullerene, as well an unit adjacent host. Femtosecond transient absorption measurements subpicosecond ultrafast charge separation (and 6) complexes. To best our knowledge, present report provides first example wherein nanographene building block incorporated into core porphyrinic framework.