Supramolecular assembly of a quasi-linear heterofullerene–porphyrin dyad

The synthesis and photophysical properties of several porphyrin (P)-phthalocyanine (Pc) conjugates (P-Pc; 1-3) are described, in which the phthalocyanines are directly linked to the β-pyrrolic position of a meso-tetraphenylporphyrin. Photoinduced energy- and electron-transfer processes were studied through the preparation of H(2)P-ZnPc, ZnP-ZnPc, and PdP-ZnPc conjugates, and their assembly through metal coordination with two different pyridylfulleropyrrolidines (4 and 5). The resulting electron-donor-acceptor hybrids, which were formed by axial coordination of compounds 4 and 5 with the corresponding phthalocyanines, mimicked the fundamental processes of photosynthesis; that is, light harvesting, the transduction of excited-state energy, and unidirectional electron transfer. In particular, photophysical studies confirmed that intramolecular energy-transfer resulted from the S(2) excited state as well as from the S(1) excited state of the porphyrins to the energetically lower-lying phthalocyanines, followed by an intramolecular charge-transfer to yield P-Pc(.+)⋅C(60)(.-). This unique sequence of processes opens the way for solar-energy-conversion processes.

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“…[1f,h, 11,[17][18][19][20][21] Such charac-teristics motivated the design of different P·C 60 and Pc·C 60 electron-donor-acceptor hybrids.…”

Section: Introductionmentioning

confidence: 99%

Porphyrin–Phthalocyanine/Pyridylfullerene Supramolecular Assemblies

Pereira

Hausmann

Tomé

et al. 2012

Chemistry A European J

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“…The formation of Mannich bases 25 results from the reaction of (C 59 N) 2 with enolizable ketones, aldehydes, and carboxylic esters (26-29) (Scheme 9.22) [42,48,49]. The reaction is reasonably interpreted in terms of the electrophilic addition of C 59 compounds 28 and 29 react with C 59 N þ in a similar manner.…”

Section: Reactions Via C 59 N Bmentioning

confidence: 86%

“…Synthesis of an Open-Cage Fullerene with an Eight-membered-ring Orifice (49) A mixture of C 60 (50 mg, 0.069 mmol) and 5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine (21 mg, 0.068 mmol) in ODCB (4 mL) was refluxed at 180 C for 17 h under an argon atmosphere. The resulting dark purple solution was directly subjected to flash column chromatography over silica gel.…”

Section: 54mentioning

confidence: 99%

Fullerene Reactivity – Fullerene Cations and Open‐Cage Fullerenes

Kitagawa¹,

Murata²,

Komatsu³

2006

Carbon‐Rich Compounds

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“…Depending on the solvent either photoinduced singlet-singlet energy transfer or electron-transfer was observed. The latter process takes place in o-dichlorobenzene as solvent and leads to the corresponding C 59 N •-π-radical anion and ZnP •+ [31].…”

Section: Fullerene-containing Systemsmentioning

confidence: 99%