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Penta(pyrenyl)[60]fullerenes: Pyrene–Pyrene and [60]Fullerene–Pyrene Interactions in the Crystal and in Solution
Author(s) -
Matsuo Yutaka,
Morita Kouhei,
Nakamura Eiichi
Publication year - 2008
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.200800122
Subject(s) - pyrene , intramolecular force , fullerene , chemistry , intermolecular force , photochemistry , fluorescence , reagent , molecule , organic chemistry , physics , quantum mechanics
A new type of fullerene–pyrene hybrid molecule, C 60 Ar 5 R [Ar=1‐pyrenyl, 4‐(1‐pyrenyl)C 6 H 4 , 4‐{(1‐pyrenyl)CO 2 }C 6 H 4 , and 4‐{(1‐pyrenyl)(CH 2 ) 3 CO 2 }C 6 H 4 ; R=H and Me] was synthesized by a regioselective penta‐addition reaction using organocopper reagents. The compounds were investigated using electrochemical measurements, DFT calculations, single‐crystal X‐ray structural analysis, and spectroscopic and fluorescence measurements. Intramolecular and intermolecular fullerene–pyrene and pyrene–pyrene interactions were characterized in the crystals. Fluorescence measurements in dilute solutions suggested the presence of intramolecular fullerene–pyrene and pyrene–pyrene interactions.