Strategic Construction of Directly Linked Porphyrin–BODIPY Hybrids

Abstract

A powerful and concise synthesis of directly linked porphyrin-BODIPY hybrids has been demonstrated, which consists of condensation of directly linked meso-pyrroyl Ni -porphyrin with arylaldehyde, oxidation with p-chloranil, and complexation with BF ⋅Et O. Synthesized hybrids include porphyrin dimer 6Ni, trimers 8Ni, 9Ni, tetramer 12Ni, pentamer 16Ni, hexamer 13Ni, and nonamers 17Ni and 18Ni. The structures of 6Ni, 9Ni and 12Ni were unambiguously confirmed by X-ray diffraction analysis. Some Ni porphyrins were effectively converted to the corresponding Zn porphryins. In these hybrids, the pigments are three-dimensionally arranged with a face-to-face dimeric porphyrin unit in a well-defined manner, featuring their potential as light-harvesting antenna and functional hosts.

Benzene- and pyridine-incorporated octaphyrins with different coordination modes toward two PdII centers

“…Recently we explored various porphyrinoids by using Suzuki-Miyaura coupling. Reported examples include cyclic porphyrin rings, BODIPY-porphyrin hybrids, and earring porphyrins [24][25][26][27][28] . Despite of these studies, we thought that this coupling strategy could be applied to the synthesis of pyridine-incorporated expanded porphyrins.…”

Conjugated BODIPY Oligomers with Controllable Near-Infrared Absorptions as Promising Phototheranostic Agents through Excited-State Intramolecular Rotations

“…These observed interesting singlet oxygen generation abilities may indicate the formation of a triplet state through the intersystem spin–orbital coupling (ISC) upon irradiation. The intramolecular rotation in the excited state populated the orthogonal orientation of neighboring BODIPY units, which triggered the formation of the ISC process similar to well-studied, directly linked orthogonal BODIPY dimers and related systems. − …”

Porphyrin‐Ryleneimide Hybrids: Low‐Bandgap Acceptors in Energy‐Transfer Cassettes

“…To address these issues, covalently connected BODIPYporphyrin hybrids have been explored by many researchers as efficient light-harvesting systems, with controllable photoinduced energy/electron transfer within the multichromophoric assembly. [11,13] Here we demonstrate the utility of ryleneimide-metalloporphyrin hybrids as acceptor units in energy transfer cassettes ( Figure 1). The parent chromophore, [14] containing four naphthalenemonoimide (NMI) units fused to a central porphyrin moiety, belongs to a recently developed family of donoracceptor (DA) oligopyrroles, [15][16][17][18][19] characterized by small electronic bandgaps, and extended redox activity.…”