Rapidly Color-Switching

Photochromic compounds

Features

pseudogem-BisDPI[2.2]paracyclophane derivatives
have excellent photochromic characteristics.

1. Rapid Color-Switching

2. High Fatigue Resistance

3. Photochromism at a Wide Range

of Temperature
 Product Introduction

Photochromic materials change their colors upon irradiation with light. The main
possible application of photochromic materials has been thought as use in optical
data storages, hologram materials and light modulators. There have been consid-
erably researches and studies about photochromic compounds.

There are 2 types of photochromic compounds, P-type and T-type. The photogener-
ated P-type compound can be converted back to its initial structure by irradiation with
a specific wavelength of light. Meanwhile, the photogenerated T-type compound can
be converted back to its initial structure thermally. However, the thermal bleach re-
action of photogenerated T-type compounds requires several minutes at room tem-
perature, and for practical use in certain applications, it demands a much faster speed
in the return to the initial state.

Hxaarylbisimidazole (HABI) was discovered in the early 1960s by Hayashi and

Maeda, and it has subsequently attracted significant interest because of its unusual
physical properties. The solution of HABI changes from colorless to purple under UV
irradiation. The thermal transformation of TPIRs to HABI requires several minutes at
room temperature.

HABI TPIRs
Kanto Chemical has commercialized pseudogem-Bis(diphenylimidazole) [2.2]
paracyclophane (1) and pseudogem-Bis(3,3’, 4,4’ - tetramethoxydiphenylimida-
zole)[2.2]paracyclophane (2) novel hexaarylbisimidazole (HABI) derivatives which
have a [2.2]paracyclophane structure. This novel compounds are originally designed
and synthesized by professor Abe from Aoyama Gakuin University. These com-
pounds have an excellent color switching character. They are colorless when dis-
solved in benzene, and change to blue or green upon UV irradiation. After the irra-
diation ceases, these color bleaches immediately.

◆ Molecular structure

１ ２
◆Photochromic reaction of 1 and 2

◆ Photochromic reaction of 1.

1 1R

◆ Photocromic reaction of 2

2 2R

◆1 and 2 dissolved in benzene change there color upon UV irradiation

１ ２

Solv.：Benzene UV irradiator：Keyence UV-400

Concentration：0.1∼0.5mM UV-LED(UV-50H) / UV-L6,
Temperature：20℃, Exciting light：(Wavelength) 355nm, (Intensity) 300mW/cm2
Quartz Cell： 1mm × 10mm × 40mm,
◆ Transient vis-NIR absoraption spectra and Decay profile of 1

Figure 1 Figure 2
Transient vis-NIR absorption spectra of 1 in de- Decay profiles of the colored species generated
gassed benzene after excitation with a nanosecond from 1, monitored at 400 nm in degassed benzene
laser pulse.(2.1 x 10-4M, 298K, recorded at 20ms (1.5×10-4M).
intervals).

1 1R

◆ The photochromic properties of a polymer film doped with

1.
A transparent amorphous polymer film of 1 also shows fast thermal bleaching of the photochromic
reaction at room temperature. Moreover, the photochromic properties of a poly(methyl methacrylate)
(PMMA) film doped with 20 wt %-1 have an excellent fatigue resistance. The practical application of 1
has been highly expected.

Figure 3
Time profiles of the transient absorbance
at 400nm of the PMMA film doped with 20
wt %-1, measured at 298K (○, freshly pre-
pared sample; ▲ , after irradiation with
10,000 laser pulses).
◆ Transient vis-NIR absoraption spectra and Decay profile of 2

Figure 4 Figure 5
Transient vis-NIR absorption spectra of 2 in de- Decay profiles of the colored species generated
gassed benzene after excitation with a nanosecond from 2, monitored at 400 nm in degassed benzene
laser pulse. (2.1 x 10-4M, 298K, recorded at 20ms (1.5×10-4M).
intervals).

2 2R

◆ Decay profiles of 1 and 2

The half-life of 1R is 33 ms at 25 ℃
The half-life of 2R is 173 ms at 25 ℃

Figure 6
Decay profiles of the colored species generated
from 1 and 2, in degassed benzene.
◆UV-Vis absorption spectrum of 1 and 2

2 shows relatively strong absorption band in the UVA radiation region.

Solv. ：benzene
Temp ：25℃

Solv ：benzene
Temp ：25℃
 Product List

Product Cat. No. Package

pseudogem-Bis(diphenylimidazole)[2.2]paracyclophane (1)

FW 672.79･46.07 / C46H34N4･C2H5OH
Purity: >98% 04425-96 100mg

04425-95 500mg

pseudogem-Bis(3,3’,4,4’-tetramethoxydiphenylimidazole)[2.2]
paracyclophane (2) 04426-68 100mg

FW 883.00 / C54H50N4O8
Purity: >98%

04426-95 500mg

Reference

1) Y. Kishimoto, J. Abe, “A Fast Photochromic Molecule That Colors Only under UV Light”,
J. Am. Chem. Soc., 131, 4227 (2009)
2) K. Mutoh, S. Hatano, J. Abe, ”An Efficient Strategy for Enhancing the Photosensitivity of
Photochromic [2.2]Paracyclophane-Bridged Imidazole Dimers” J. Photopolym. Sci. Technol.,
23, 301 (2010)
 Relative Products －Diarylethene－

Kanto Chemical has commercialized a typical P-type photochromic compound, diarylethene, which
was developed by professor Irie from Rikkyo University.

Product Cat. No. Package

1,2-Bis(2-methylbenzo[b]thiophene-3-yl)perfluorocyclopentene (3a)
05058-63 100mg
FW 468.48 / C23H14F6S2
Purity: >96% 05058-96 500mg

F F F F
F F F F
F F F F

CH3 ‘ CH3

S H 3C S S H3 C S

3a Colorless 3b Red

April. 2012