Novel aromatic polyamides containing 2‐diphenylamino‐(9,9‐dimethylamine) units as multicolored electrochromic and high‐contrast electrofluorescent materials

Abstract

A series of electrochromic and photoluminescenceactive polyamides 4a-4e were prepared from a novel dicarboxylic acid, N,N-di(4-carboxyphenyl)-2-amino-9,9-dimethylfluorene, and five diamines via a condensation polymerization. These polyamides were amorphous and readily soluble in many solvents. The glass transition temperatures were in the range of 281-339 8C and the 10% weight loss temperatures in nitrogen were in excess of 490 8C. The polyamides exhibited strong fluorescence in either solution or solid states. The polyamides 4a-4d showed reversible electrochemical redox with color changing from colorless to grey-green. Specially, the polyamide 4e with 2-diphenylamino-(9,9-dimethylamine) group in both diamine and dicarboxylic acid residues exhibited multicolored electrochromic behaviors. Furthermore, the fluorescence of these polyamides could be reversibly electroswitched with a high contrast up to 221.4, enabling their potential applications in dual-switching electrochromic/electrofluorescent materials. V C 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 213-222

Synthesis and electrochemical characterization of polyamic acid containing oligoaniline and triphenylamine

“…Multi‐color electrochromic devices can be readily fabricated through molecular design and functional control. It is worthwhile mentioning that some fluorescent triphenylamine‐based polymers have recently been designed and prepared . The resulting polymers exhibit an exciting electrochromic and electrofluorescent dual‐switching behavior, which suggests their promising applications in displays and sensors.…”

Functional Aromatic Polyamides

“…In this section of our review we summarize the works published in this research field by Hsiao and coworkers , Sun et al [126] and He et al [127]. Electrochromic aramids are principally In this section of our review we summarize the works published in this research field by Hsiao and coworkers , Sun et al [126] and He et al [127].…”

“…Electrochromic aramids are principally In this section of our review we summarize the works published in this research field by Hsiao and coworkers , Sun et al [126] and He et al [127]. Electrochromic aramids are principally based on the polymerization of monomers that contain sub-structures that are the responsible for the reversible electrochemical oxidation processes accompanied with strong color changes of the polymer films prepared by casting, spin-coating or electropolymerization.…”

“…The optical transmittance change between the neutral and the fully oxidized states was up to 83% (at 636 nm) [106]. -- [121] 3,6-dimethoxycarbazole [112,122] 3,6-di-tert-butylcarbazole [96,101,103] methyl, trifluoromethyl [104] 4-tert-butyl [99,[116][117][118] 2,4-dimethoxy [102] adamantylphenoxy [105] --ether-linked bis(triphenylamine) [106] piperidinyl [108] morpholinyl [97] TPA (pendant) -- [107,109,113] TPA or carbazole electrompolymerization [110,124,125] diphenylpyrenylamine [98] carbazole methoxy [114] carbazole (pendant) [119,120,123] N,N,N′,N′-tetraphenyl-1,4-phenylenediamine, TPPA tert-butyl [111] methoxy [100] bis(diphenylamino)naphthalene metoxy [126] diphenylfluorenylamine methyl [127] aniline pentamer/azo group…”

“…[105] -ether-linked bis(triphenylamine) [106] piperidinyl [108] morpholinyl [97] TPA (pendant) - [107,109,113] TPA or carbazole electrompolymerization [110,124,125] diphenylpyrenylamine [98] carbazole methoxy [114] carbazole (pendant) [119,120,123] N,N,N ,N -tetraphenyl-1,4-phenylenediamine, TPPA tert-butyl [111] methoxy [100] bis(diphenylamino)naphthalene metoxy [126] diphenylfluorenylamine methyl [127] aniline pentamer/azo group based on the polymerization of monomers that contain sub-structures that are the responsible for the reversible electrochemical oxidation processes accompanied with strong color changes of the polymer films prepared by casting, spin-coating or electropolymerization. These electroactive groups are mainly triphenylamine (TPA), N,N,N′,N′-tetraphenyl-1,4-phenylenediamine (TPPA), diphenylpyrenylamine, bis(diphenylamino)naphthalene, diphenylfluorenylamine, and carbazole ( Table 3).…”