A Bis(C₆₀)–Bis(phthalocyanine) Nanoconjugate: Synthesis and Photoinduced Charge Transfer

Abstract

A novel dimeric phthalocyanine-C60 nanoconjugate, consisting of a bisphthalocyanine core to which two fullerenes are attached, has been prepared. The synthetic strategy implemented the preparation of a diformyl butadiynyl-bridged bisphthalocynaninato-zinc(II) complex by means of palladium-catalyzed cross-coupling reactions and subsequent dipolar cycloaddition reactions. Photophysical experiments confirm that an intramolecular electron transfer, namely, from the photoexcited ZnPc moiety to the electron-accepting C60 unit, governs the overall photoreactivity of the nanoconjugate. Through-space charge-transfer interactions facilitated by the close proximity of the ZnPc and the C60 moieties play a decisive role in determining the lifetimes of the charge-separated state which range from 10(-10) to 10(-9) seconds.

Phthalocyanine−Pyrene Conjugates: A Powerful Approach toward Carbon Nanotube Solar Cells

“…In detail, for ZnPc and ZnPc-Py, new bands are discernible in the 400−600 nm range and around 840 nm. These are the well-known fingerprints of the one-electron-oxidized form of ZnPc (see Supporting Information, Figure S1) . For H 2 Pc and H 2 Pc-Py, a broad absorption in the 400−600 nm range (i.e., H 2 Pc, maxima at 405 and 535 nm; H 2 Pc-Py, maximum at 490 nm) is observable; additionally, we can identify a band around 900 nm for both metal-free phthalocyanines.…”

A voyage into the synthesis and photophysics of homo- and heterobinuclear ensembles of phthalocyanines and porphyrins

“…Binuclear conjugate 25 was then reacted with N-methyl glycine and C 60 to afford Pc 2 -(C 60 ) 2 tetrad 24 (Scheme 7). 83 Regarding the incorporation of alkenyl linkers for the fabrication of binuclear Pc-Pc-based multicomponent systems, Heck-type coupling proved successful to form triads 27-29 (Fig. 5), consisting of one AQ unit covalently linked to two Zn(II)Pcs.…”

“…The photophysical properties of multicomponent Zn(II)Pc 2 -(C 60 ) 2 nanoconjugates 24 (Scheme 7) have also been investigated. 83 Steady state fluorescence assays, in which different solvent polarities were probed, reveal that quenching of the Pc fluorescence takes place, which is due to intramolecular electron transfer. This process is accelerated in polar media, although the quantum yield of CS is reduced.…”

Network assembly of gold nanoparticles linked through fluorenyl dithiol bridges

“…The synthesis of uorenyl thiolate (2) bearing two ethynylphenyl spacers between uorene and the terminal thioacetyl groups has been carried out (see ESI †). The rst step consisted in a Sonogashira coupling reaction of 9,9-didodecyl-2,7-dibromo-uorene with 2 equivalents of trimethylsilylacetylene (TMSA) to give 1a in 73% yield, according to literature reports for similar compounds, [22][23][24][25][26][27][28] followed by deprotection of the triple bonds to give compound 1b in 90% yield. The last step in the synthesis of the target compound 2 required the use of 1-(S-acetylthio)-4iodobenzene, since all attempts to couple 1b with commercially available 4-bromophenylthioacetate failed.…”