Donor−Acceptor Nanohybrids of Zinc Naphthalocyanine or Zinc Porphyrin Noncovalently Linked to Single-Wall Carbon Nanotubes for Photoinduced Electron Transfer

In this review, we report the recent advances in the construction of composite molecular nanoarchitectures of porphyrins and nanoscale carbon materials such carbon nanotubes (CNT), graphenes and polycyclic aromatic hydrocarbons (PAH) for photoinduced electron transfer and light energy conversion. First, we state novel single-wall carbon nanotubes (SWCNT)-driven aggregation of protonated porphyrins to produce supramolecular assemblies in the form of macroscopic bundles. Then, photoinduced electron transfer in self-assembled single-walled carbon nanotube (SWCNT)/zinc porphyrin (ZnP) hybrids utilizing (7,6)- and (6,5)-enriched SWCNTs having different band gaps is reported. Further, we discuss the structural and photoelectrochemical properties of porphyrin-based molecular assemblies of other carbon materials such as stacked-cup carbon nanotubes (SCCNT), carbon nanohorns (CNH) and graphenes. Finally, novel supramolecular patterning formation composed of triphenylene core-centered porphyrin hexamers for electronics is discussed.

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Naphthalenebisimides as photofunctional surfactants for SWCNTs – towards water-soluble electron donor–acceptor hybrids

Chemical Science ◽

10.1039/c5sc02944a ◽

2015 ◽

Vol 6 (12) ◽

pp. 6886-6895 ◽

Cited By ~ 13

Author(s):

Konstantin Dirian ◽

Susanne Backes ◽

Claudia Backes ◽

Volker Strauss ◽

Fabian Rodler ◽

...

Keyword(s):

Carbon Nanotubes ◽

Electron Donor ◽

Water Soluble ◽

Single Wall Carbon Nanotubes ◽

Single Wall Carbon ◽

Donor Acceptor

A water soluble naphthalenebisimide derivative (NBI) was synthesized and probed to individualize, suspend, and stabilize single wall carbon nanotubes (SWCNT).

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Photoinduced electron transfer in a directly linked meso-triphenylamine zinc porphyrin-quinone dyad

Journal of Porphyrins and Phthalocyanines ◽

10.1142/s108842461100329x ◽

2011 ◽

Vol 15 (05n06) ◽

pp. 391-400 ◽

Cited By ~ 7

Author(s):

Channa A. Wijesinghe ◽

Marja Niemi ◽

Nikolai V. Tkachenko ◽

Navaneetha K. Subbaiyan ◽

Melvin E. Zandler ◽

...

Keyword(s):

Electron Transfer ◽

Photoinduced Electron Transfer ◽

Free Energy Calculations ◽

Excitation Wavelength ◽

Triplet States ◽

Time Resolved ◽

Zinc Porphyrin ◽

Porphyrin Macrocycle ◽

Donor Acceptor ◽

Donor Ability

A multimodular donor-acceptor system composed of three triphenylamine entities at the meso-positions of a zinc porphyrin macrocycle and a quinone at the fourth meso-position was newly synthesized and characterized. The triphenylamine entities acted as energy transferring antenna units in addition of improving the electron donor ability of the zinc porphyrin. Appreciable electronic interactions of the triphenylamine and quinone entities with the porphyrin π-system were observed. In agreement with the spectral and electrochemical results, the computational studies performed by the DFT B3LYP/3-21G(*) method revealed delocalization of the frontier HOMO over the triphenylamine and the porphyrin macrocycle while the LUMO to be fully localized over the quinone entity. Free-energy calculations suggested photoinduced electron transfer from the singlet excited zinc porphyrin to the directly linked quinone to be exothermic and this was experimentally confirmed by the time-resolved pump probe and up-conversion techniques. In the investigated system, the ET reaction path was found to depend upon the excitation wavelength. That is, when Zn porphyrin was predominantly excited, a rapid charge separation followed by equally fast charge recombination was observed. However, excitation of the peripheral TPA substituents resulted in an extremely long-lived CS state with triplet spin character via the TPA triplet and Zn porphyrin triplet states.

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