Electron-accepting phthalocyanine–pyrene conjugates: towards liquid phase exfoliation of graphite and photoactive nanohybrid formation with graphene

Abstract

Herein, we describe the synthesis of a zinc(II) alkylsulfonylphthalocyanine-pyrene conjugate, its assembly with highly exfoliated graphite, and the investigation of the photophysical properties of the resulting nanohybrid. The presence of the pyrene unit in the conjugate is decisive in terms of non-covalently immobilizing the electron accepting phthalocyanines onto the basal plane of highly exfoliated graphite.As a matter of fact, strong interactions dominate the electronic properties of the nanohybrid in both the ground and excited states. For example, femtosecond pump probe experiments assist in corroborating an ultrafast charge separation, that is, the generation of the one-electron reduced radical anion of the phthalocyanine and one-electron oxidized graphene after irradiation at 387 nm, followed by slow charge recombination.

Combining Electron‐Accepting Phthalocyanines and Nanorod‐like CuO Electrodes for p‐Type Dye‐Sensitized Solar Cells

“…[13,14] Key merits of porphyrins, and specially of their synthetic related phthalocyanines , (Pcs), [15,16] are their exceptional light-harvesting features and their facile functionalization with either electrondonors or electron-acceptors, underlining their potential for DSSCs. In light of the latter, tuning the physicochemical features of phthalocyanines towards new electron-accepting dyes [17,18] by means of placing electron-withdrawing substituents at their periphery, complements, in the current work, our research regarding nanorod-like CuO electrodes. [19] ; ii) IBX, DMSO/THF; iii) H3NSO3/H2O followed by NaClO2; iv) propargyl alcohol, Pd(PPh3)2Cl2, CuI, NEt3, THF Notably, the synergy of nanorod-like CuO DSSCs and electronaccepting Pcs enables the construction of p-DSSCs with efficiencies as high as 0.103% and 0.191% with iodine-and cobalt-based electrolytes, respectively.…”

Combining Electron‐Accepting Phthalocyanines and Nanorod‐like CuO Electrodes for p‐Type Dye‐Sensitized Solar Cells

“…[13,14] Key merits of porphyrins, and specially of their synthetic related phthalocyanines , (Pcs), [15,16] are their exceptional light-harvesting features and their facile functionalization with either electrondonors or electron-acceptors, underlining their potential for DSSCs. In light of the latter, tuning the physicochemical features of phthalocyanines towards new electron-accepting dyes [17,18] by means of placing electron-withdrawing substituents at their periphery, complements, in the current work, our research regarding nanorod-like CuO electrodes. ; ii) IBX, DMSO/THF; iii) H3NSO3/H2O followed by NaClO2; iv) propargyl alcohol, Pd(PPh3)2Cl2, CuI, NEt3, THF Notably, the synergy of nanorod-like CuO DSSCs and electronaccepting Pcs enables the construction of p-DSSCs with efficiencies as high as 0.103% and 0.191% with iodine-and cobalt-based electrolytes, respectively.…”

Coordination chemistry on carbon surfaces

“…Solution mixing in THF UV-vis, fluorescence, SEM, AFM Photoinduced electron transfer; prototype solar cell [191] pyrene-tagged ligands can be used to improve the anchoring process [192], to avoid a modification of the electronic properties of one of the component of the resulting hybrid system [197] or to increase the stabilization of graphene sheets formed upon ultrasonication induced exfoliation [195]. In any cases, the noncovalent approaches is particularly valuable for applications in charge transfer/separation where it is highly desirable to keep as much as possible intact the integrity of the CNTs or graphene aromatic network and therefore its intrinsic conducting properties.…”

“…Some reports also mention the use of pyrene moieties to immobilize on SWCNTs or graphene surfaces metallomacrocycles like porphyrines or phthalocyanines (see Table 11) [163,[189][190][191][192][193][194][195][196], mainly for the preparation of donor-acceptor hybrid systems for photoinduced electron transfer. Generally, 1D or 2D sp 2 carbon nanomaterials are employed as electron acceptors in association with excited state electron donors.…”