Methyl-substituted Derivatives of 1,3,5-Tris(diphenylamino)benzene as a Novel Class of Amorphous Molecular Materials

Abstract

Methyl-substituted derivatives of 1,3,5-tris(diphenylamino)benzene (TDAB) are found to show unique solid-state morphology, as characterized by differential scanning calorimetry and X-ray diffraction. These compounds readily form stable amorphous glasses having glass-transition temperatures of ca. 50 °C. p-Methyl-substituted TDAB exhibits polymorphism.

Synthesis and Characterization of Calix[4]resorcinearene Bearing Azobenzene Moieties as Novel Photofunctional Materials.

“…Calix [4]resorcinearene bearing azobenzene moieties (CAAB) was prepared by the etherification reaction of calix [4]resorcinearene with 4-[4-(6-bromohexyloxy)phenylazo]nitrobenzene. Characterization of the product by MALDI TOF-MS analysis, and 'H-NMR analysis supported the formation of compleately CAAB.…”

“…These results indicate that the aggregation of CAAB is suppressed in PVK matrix, and the 2nd-NLO susceptibility of the CAAB is larger than that of the AB, even at the same doping level. This may be due to the all-cis structure of the calix [4]resorcinearene.…”

“…Shirota et al [4] have recently suggested a new guideline for molecular design of low molecular weight amorphous materials, named "amorphous molecules". In addition, a definite molecule weight and a good processability of "amorphous molecules"…”

“…The introduction of azobenzene chromophores to calix [4]resorcinearene was expected to provide "amorphous molecules" for photofunctional materials such as 2nd-NLO properties. Sample preparation of calix [4]resorcinearene bearing azobenzene moieties (CAAB) and 4-(4-hydroxyphenylazo)nitrobenzene (AB) were carried out under the following three conditions.…”

Vapochromic Fluorescence Observed for Emitting Amorphous Molecular Materials: Synthesis and Emitting Properties of 3-{4-[Bis(4-methylphenyl)amino]phenylcarbonyl}-6-{4-[bis(4-methylphenyl)amino]phenyl}-3,5-dimethyl-3,4-dihydro-2H-pyran

“…We have been made a part of studies of the creation of organic low molecular-mass materials that readily form amorphous glasses, namely amorphous molecular materials [12][13][14][15][16], and in due course we have found that 4-[bis(4-methylphenyl)-amino]benzaldehyde (BMABA) and 4-[bis(4-methylphenyl)amino]acetophenone (BMAAP) exhibited solvatochromic fluorescence, mechanochromic fluorescence [17,18], AIE [19,20], and vapochromic fluorescence [21]. …”