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Facile Synthesis and Photophysical Properties of Sphere–Square Shape Amphiphiles Based on Porphyrin–[60]Fullerene Conjugates
Author(s) -
Wang ChienLung,
Zhang WenBin,
Yu Xinfei,
Yue Kan,
Sun HaoJun,
Hsu ChihHao,
Hsu ChainShu,
Joseph Jojo,
Modarelli David A.,
Cheng Stephen Z. D.
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201201089
Subject(s) - amphiphile , porphyrin , quenching (fluorescence) , fullerene , fluorescence , chemistry , photochemistry , molecule , excited state , derivative (finance) , combinatorial chemistry , materials science , organic chemistry , copolymer , polymer , physics , quantum mechanics , nuclear physics , financial economics , economics
Molecules constructed from a combination of zero‐dimensional ([60]fullerene (C 60 )) and two‐dimensional (porphyrin (Por)) nanobuilding blocks represent an intriguing category of sphere–square “shape amphiphiles”. These sphere–square shape amphiphiles possess interesting optoelectronic properties. To efficiently synthesize a large variety of C 60 –Por shape amphiphiles, a facile route based on Steglich esterification was developed. The synthetic strategy enables the preparation of hydroxy‐functionalized Por precursors ( 9 , 10 , 11 , 12 ) with high purity in a one‐pot procedure . All of the C 60 –Por shape amphiphiles ( 1 , 2 , 3 , 4 , 5 ) can be readily synthesized in good yields through subsequent Steglich esterification with a highly soluble carboxylic acid derivative of methanofullerene ( 13 ). Photophysical studies indicated weak electronic coupling between the C 60 and Por moieties and suggest an edge‐to‐face alignment for the moieties. The fluorescence of electronically excited Por portions of each amphiphile was efficiently quenched, which was indicative of electron transfer from 1 Por to the C 60 group(s). Increasing the number of C 60 groups on the shape amphiphiles led to more pronounced quenching of the Por fluorescence, which indicated the potential for more effective generation of charge‐separated species, C 60 −. Por +. , from the photoexcited C 60 –Por shape amphiphiles.