Solution‐processable and electroactive aromatic polyamides with 3,5‐bis(trifluoromethyl)triphenylamine moiety

Abstract

New fluorine‐containing, triphenylamine‐based diamine and dicarboxylic acid monomers, namely 3,5‐bis(trifluoromethyl)‐4′,4″‐diaminotriphenylamine and 3,5‐bis(trifluoromethyl)‐4′,4″‐dicarboxytriphenylamine, were synthesized and polymerized with commercially available aromatic dicarboxylic acids and diamines, respectively, leading to two series of aromatic polyamides, 5a–h and 7a–e. Most of the polyamides were amorphous and readily soluble in many common organic solvents and could be solution‐cast into transparent, flexible and strong films with good mechanical properties. The polyamides had useful levels of thermal stability associated with high glass transition temperatures of 273–305 °C and 10% weight‐loss temperatures in excess of 500 °C. Cyclic voltammograms of films of polymers 5a–h on indium–tin oxide‐coated glass substrates exhibited reversible oxidation redox couples with E1/2 around 1.15 V versus Ag/AgCl in tetrabutylammonium perchlorate/acetonitrile solution, accompanied by a color change from colorless neutral state to reddish brown oxidized state. The 7 series polymers displayed a higher oxidation potential and less electrochemical stability as compared to the 5 series analogues. © 2017 Society of Chemical Industry

Functional Aromatic Polyamides

“…In this section of our review we summarize the works published in this research field by Hsiao and coworkers [ 96 , 97 , 98 , 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 , 107 , 108 , 109 , 110 , 111 , 112 , 113 , 114 , 115 , 116 , 117 , 118 , 119 , 120 , 121 , 122 , 123 , 124 , 125 ], 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…”

“…Main electroactive group Auxiliary EDG or EWG Comments [41] triphenylamine, TPA -hyperbranched [115] - [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…”

Synthesis of new fluorinated aromatic poly (ether ketone amide)s containing cardo structures by a heterogeneous palladium‐catalyzed carbonylative polycondensation

“…Very recently, we reported the synthesis of a magnetic nanoparticle‐supported bidentate phosphine palladium (II) complex [Fe 3 O 4 @SiO 2 ‐2P‐PdCl 2 ] and its successful application to the carbonylative polycondensation of aromatic diiodides with ether ketone units, aromatic diamines bearing pyridine groups, and carbon monoxide leading to novel aromatic poly (ether ketone amide)s containing 4‐aryl‐2,6‐diphenylpyridine units . It has been demonstrated that the incorporation of fluorinated groups into polyamide backbones can provide not only enhanced solubility but also improved electrical and dielectric performance . Recently, the synthesis of fluorinated polyamides containing cardo structures has attracted considerable interest because of their excellent combined properties .…”

“…45 It has been demonstrated that the incorporation of fluorinated groups into polyamide backbones can provide not only enhanced solubility but also improved electrical and dielectric performance. [47][48][49][50][51][52][53][54] Recently, the synthesis of were synthesized according to the reported method. 47 The magnetic nanoparticle-supported bidentate phosphine palladium (II) complex [Fe 3 O 4 @SiO 2 -2P-PdCl 2 ] was prepared by our previous procedure.…”