Communication
ChemComm
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Furthermore, we confirmed that the presence of molecular
oxygen has no influence on the half-life of the colored species
of 1a and only a slight influence on the fatigue resistance as
shown in Fig. 3.
In conclusion, we developed a new type of fast photochromic
imidazole dimer, PABI. PABI derivatives are easy to synthesize
and show fast photochromism in a ms time scale. It was revealed
that the electronic structures of the colored species of PABI
derivatives are similar to that of o-QDM. This is the first report
of reversible generation of the o-QDM structure, which is an
important species in physical and synthetic chemistry. We found
that the introduction of the electron-donating methoxy groups on
the phenylene effectively stabilizes the colored species, resulting
in the prolonged half-life of the colored species 1bR. Moreover,
PABI derivatives have the high fatigue resistance against light
irradiation. We believe that PABI derivatives become widely
applicable photoswitching systems in the field of fundamental
research and practical applications.
¨
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This work was supported partly by the Core Research for the
Evolutional Science and Technology (CREST) program of the
Japan Science and Technology Agency (JST) and a Grant-in-Aid for
Scientific Research (A) (22245025) from the Ministry of Education,
Culture, Sports, Science and Technology (MEXT), Japan.
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36 Crystallographic data for (a) 1aL: C36H26N4, Mr = 514.61; triclinic;
%
space group P1; a = 9.0514(11), b = 12.8065(11), c = 12.8890(15) Å; a =
98.181(1)1, b = 107.151(1)1, g = 103.624(1)1; V = 1350.9(3) Å3; rcalcd
=
1.260 g cmꢀ3; Z = 2; R1 = 0.0459 [I 4 2.0s(I)], wR2 = 0.0660 (all data),
GOF = 1.322 (data/restrain/params = 5844/0/370). CCDC 999576;
(b) 1a: C36H24N4, Mr = 512.59; orthorhombic; space group Pna21;
a = 15.8279(16), b = 13.8209(7), c = 14.2201(7) Å; a = 901, b = 901,
g = 901; V = 2693.1(5) Å3; rcalcd = 1.264 g cmꢀ3; Z = 4; R1 = 0.0396
[I 4 2.0s(I)], wR2 = 0.0890 (all data), GOF = 1.034 (data/restrain/
params = 4290/1/362). CCDC 999577.
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