Striking effects of halogen substituents on the glass-forming properties, glass-transition temperatures and stabilities of the glassy state of a new family of amorphous molecular materials, 1,3,5-tris(4-halogenophenylphenylamino) benzenes

Abstract

A new class of n-electron starburst molecules, 1,3,5-tris(4halogenophenylphenylamino) benzenes, are synthesized for use as amorphous molecular materials. It was found that they readily form amorphous glasses, whereas the parent compound 1,3,5-tris(diphenylamino) benzene instantly crystallizes and that the ease of glass formation, glasstransition temperature, and stability of the glassy state are greatly affected by the type of halogen substituent.

Synthesis and photoinduced surface relief grating formation of novel photo-responsive amorphous molecular materials, 4-[bis(9,9-dimethylfluoren-2-yl)amino]-4′-cyanoazobenzene and 4-[bis(9,9-dimethylfluoren-2-yl)-amino]-4′-nitroazobenzene

“…When the glasses were again heated, baseline shifts due to a glass-transition were observed at 116 C and 117 C, respectively, being higher than the Tg of the parent material, BFlAB (97 C). On further heating, no crystallization phenomena were observed, suggesting that the amorphous glasses were fairly stable [38].…”

Synthesis and Electrochemical Properties of Novel 1,3,5-Tris(oligothienyl)benzenes: A New Generation of 3D Reticulating Agents

“…For example, new amorphous molecular materials with large electroluminescent or electrochromic effects [2] can be developed around 1,3,5-tris(aryl)benzene or 1,3,5-tris(aryl-thienyl)benzene centers. Furthermore, all these properties are improved by the introduction of terminal alkyl [4] or bromine [5] substituents. In addition, oligothiophenes are very promising materials for the development of all these devices.…”

Synthesis and Properties of Novel Derivatives of 1,3,5-Tris(diarylamino)benzenes for Electroluminescent Devices

“…The absorption, fluorescence, electrochemical behavior, and thermal properties of these materials were investigated. Differential scanning calorimetry (DSC) measurements revealed that these new aryl derivatives possess higher T g s compared to the known phenyl derivatives [14,15] and the crystalline compound hexaanisyl-1,3,5-triaminobenzene. [16] Cyclic voltammetry (CV) measurements showed that these compounds have high HOMO values in the range ±5.07 to ±5.16 eV.…”

“…The compounds 4c, 4d, and 4e have T g values of 85 C, 91 C, and 123 C, respectively, which are higher than those reported for halogen-or methyl-substituted phenyl derivatives of TDABs. [14,15] Though the amorphous nature of the vapor-deposited films can be verified only by analyzing the solid-state morphology of such films, we assume that the compounds 4b, 4d, and 4e are suitable materials for vapor deposition to obtain amorphous films. LED Results: To our knowledge, LED results using the reported phenyl derivatives [14±16] as hole-transport materials have not been previously published.…”