Creation of azobenzene-based photochromic amorphous molecular materials—synthesis, glass-forming properties, and photochromic response

Tanino, Takahiro; Yoshikawa, Satoru; Ujike, Toshiki; Nagahama, Daisuke; Moriwaki, Kazuyuki; Takahashi, Tôru; Kotani, Yoshiko; Nakano, Hideyuki; Shirota, Yasuhiko

doi:10.1039/b711542c

Cited by 66 publications

(67 citation statements)

References 52 publications

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“…The Tg was determined to be 19 °C by DSC, which was considerably lower than that of the parent material, 4-[di(biphenyl-4-yl)amino]azobenzene (68 °C) [24]. The existence of the flexible long alkyl chain is assumed to reduce the Tg.…”

Section: Resultsmentioning

confidence: 99%

Photoinduced Surface Relief Grating Formation Using Mixed Amorphous Films of Molecular Materials: 4-[4'-Stearoyloxybiphenyl-4-yl(biphenyl-4-yl)-amino]azobenzene-4,4',4''-Tris[3-methylphenyl-(phenyl)amino]triphenylamine System

Nakano

Yoshitake

2011

J. Photopol. Sci. Technol.

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photoinduced SRG formation using a mixed film of DBAB-St and m-MTDATA has been investigated. ExperimentalDBAB-St was synthesized as follows: stearoyl chloride (0.70 g, 2.3 mmol) was added to a THF solution (20 mL) of 4-[4'-hydroxybiphenyl-4-yl(biphenyl-4-yl)amino]azobenzene (DBAB-OH: 1.0 g, 1.9 mmol), prepared by the procedure reported in our previous paper [ 23 ], and triethylamine (0.39 g, 3.9 mmol), and then the solution was stirred for 2 h at room temperature. After the solvent was removed under reduced pressure, the product was purified by silica-gel column chromatography using toluene as an eluent, followed by recrystallization from ethanol. Yield: 0.78 g (52%), m. Differential scanning calorimetry (DSC) was carried out by means of DSC6220 (Seiko Instruments Inc.) Photoinduced SRG formation was carried out by using a compact CW laser (488 nm: CYAN-488-100NH-W, Spectra Physics) as a source of writing beams. Atomic force microscopy (AFM) was performed by means of Scanning Probe Microscope (JSTM-4200D, JEOL Ltd.) with a micro cantilever (OMCL-AC160T-C2, Olympus). Results and discussionA novel photochromic amorphous molecular material, DBAB-St, was synthesized by the reaction of DBAB-OH with stearoyl chloride in the presence of triethylamine and identified by various spectroscopy and mass spectrometry (Scheme 1). DBAB-St was found to readily form an amorphous glass when the melt sample was cooled on standing in air.The Tg was determined to be 19 °C by DSC, which was considerably lower than that of the parent material, 4-[di(biphenyl-4-yl)amino]azobenzene (68 °C) [24]. The existence of the flexible long alkyl chain is assumed to reduce the Tg. The Tg of DBAB-St was found to be increased by mixing with m-MTDATA; the Tg of the mixed glass of DBAB-St and m-MTDATA with a ratio of 1:4 (w/w) was determined to be 48 °C.Using the amorphous films of DBAB-St and the mixed film of DBAB-St and m-MTDATA with a ratio of 1:4 (w/w), photoinduced SRG formation was investigated. The amorphous films were irradiated with two writing beams (488 nm) with incident angles of +10° and -10° with respect to the normal of the sample film and with polarization angles of +45° and -45° with respect to the p-polarization at 3 mW (ca. 95 mWcm -2 ) each (Fig. 1). J. Photopolym. Sci. Technol., Vol. 24, No. 5, 2011 528 Fig . 2 shows the growth of diffraction efficiency upon irradiation with writing beams at 20 °C.Whereas significant increase in diffraction efficiency could not be observed for the DBAB-St amorphous film upon irradiation with the writing beams, the diffraction efficiency gradually increased and reached to ca. 7% in 30 min for the mixed film of DBAB-St and m-MTDATA. In addition, SRG with a modulation depth of 170-190 nm was confirmed to be inscribed on the mixed amorphous film by means of AFM as shown in Fig. 3. Thus, the mixing with m-MTDATA drastically enhanced the SRGforming ability of DBAB-St.As discussed in our previous paper [13], the increasing Tg of the material prevents the collapse of the SRG due to surface tension to...

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Section: Resultsmentioning

confidence: 99%

Photoinduced Surface Relief Grating Formation Using Mixed Amorphous Films of Molecular Materials: 4-[4'-Stearoyloxybiphenyl-4-yl(biphenyl-4-yl)-amino]azobenzene-4,4',4''-Tris[3-methylphenyl-(phenyl)amino]triphenylamine System

Nakano

Yoshitake

2011

J. Photopol. Sci. Technol.

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“…Among these, azobenzne-based photochromic amorphous molecular materials were found to exhibit trans-cis photo-isomerization reactions as amorphous films as well as in solutions [15,18]. In addition, several photomechanical effects of azobenzene-based photochromic amorphous molecular materials and crystalline materials caused by photoinduced mass transport have been found [20][21][22][23][24][25][26][27][28][29].…”

Section: Open Accessmentioning

confidence: 99%

“…BMAB, DBAB, BFlAB, and NO 2 -BFlAB were prepared according to our previous papers [18,24]. Glass transition temperatures (Tg) of BMAB, DBAB, BFlAB, and NO 2 -BFlAB were 27 °C, 68 °C, 97 °C, and 117 °C, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…We have been performing studies of the creation of a low molecular-mass photochromic compound which readily form amorphous glasses, namely "photochromic amorphous molecular materials" [15][16][17][18][19]. Among these, azobenzne-based photochromic amorphous molecular materials were found to exhibit trans-cis photo-isomerization reactions as amorphous films as well as in solutions [15,18].…”

Section: Open Accessmentioning

confidence: 99%

“…30 μm). From the extinction coefficient of the present materials [18,25], penetration depth of the incident laser beam into the fiber was estimated to be ca. 100-200 nm, considerably smaller than the diameter of the fiber.…”

Section: Photoinduced Bending Motions Of Molecular Fibersmentioning

confidence: 99%

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Photomechanical Bending of Azobenzene-Based Photochromic Molecular Fibers

2013

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Microfibers composed of azobenzene-based photochromic amorphous molecular materials, namely low molecular-mass photochromic materials with a glass-forming property, could be fabricated. These fibers were found to exhibit mechanical bending motion upon irradiation with a laser beam. In addition, the bending direction could be controlled by altering the polarization direction of the irradiated light without changing the position of the light source or the wavelength of the light. In-situ fluorescence observation of mass transport induced at the surface of the fiber doped with CdSe quantum dots suggested that the bending motions were related with the photoinduced mass transport taking place near the irradiated surface of the fiber.

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