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Self‐Assembled Single‐Walled Carbon Nanotube:Zinc–Porphyrin Hybrids through Ammonium Ion–Crown Ether Interaction: Construction and Electron Transfer
Author(s) -
D'Souza Francis,
Chitta Raghu,
Sandanayaka Atula S. D.,
Subbaiyan Navaneetha K.,
D'Souza Lawrence,
Araki Yasuyuki,
Ito Osamu
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700583
Subject(s) - crown ether , carbon nanotube , porphyrin , electron transfer , ammonium , materials science , brush , ion , zinc , nanotechnology , inorganic chemistry , photochemistry , chemistry , organic chemistry , composite material , metallurgy
An ammonium ion–crown ether interaction has been successfully used to construct porphyrin–single‐walled carbon nanotube (SWNT) donor–acceptor hybrids. The [18]crown‐6 to alkyl ammonium ion binding strategy resulted in porphyrin–SWNT nanohybrids that are stable and soluble in DMF. The porphyrin–SWNT hybrids were characterized by spectroscopic, TEM, and electrochemical techniques. Both steady‐state and time‐resolved emission studies revealed efficient quenching of the singlet excited state of the porphyrins and free‐energy calculations suggested that electron‐transfer quenching occurred. Nanosecond transient absorption spectral results supported the charge‐separation quenching process. Charge‐stabilization was also observed for the nanohybrids in which the lifetime of the radical ion pairs was around 100 ns. The present nanohybrids were also used to reduce the hexyl viologen dication (HV 2+ ) and to oxidize 1‐benzyl‐1,4‐dihydronicotinamide in solution in an electron‐pooling experiment. Accumulation of the radical cation (HV .+ ) was observed in high yields, which provided additional proof for the occurrence of photoinduced charge separation. The present study demonstrates that a hydrogen‐bonding motif is a successful self‐assembly method to build SWNTs bearing donor–acceptor nanohybrids, which are useful for light‐energy harvesting and photovoltaic applications.