Immobilized polyazomethines containing triphenylamine groups on ITO: synthesis and acidochromic, electrochemical, electrochromic and photoelectronic properties

Ma, Xiaochuan; Wu, Yanshuang; Wen, Hailin; Niu, Haijun; Wang, Cheng; Qin, Chuanli; Bai, Xuduo; Lei, Lei; Wang, Wen

doi:10.1039/c5ra22918a

Cited by 34 publications

(27 citation statements)

References 52 publications

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“…The second bands are partially overlapped with the first bands and look like small shoulders centered at 342 nm. These signals were assigned to n– π * transitions of the nitrogen lone pair on the imine unit . Both PAzMCs showed a solvatochromism effect with a red shift of approximately 13 nm (bathochromic shift) for the π – π * transition bands when DMSO was used as a solvent instead of THF.…”

Section: Resultsmentioning

confidence: 99%

New cardo silylated poly(azomethine)s containing 9,9′‐diphenylfluorene units as materials with Brønsted acid‐dependent fluorescence

Hauyon

Garrido‐Gatica

Sobarzo

et al. 2019

Polymer International

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Aromatic poly(azomethine)s have been studied due to their attractive properties such as high thermal stability, semiconducting behavior and the ability to coordinate species with their imine units (CN). In this paper, the synthesis and characterization of two novel silylated poly(azomethine)s containing cardo units are reported. These materials were highly soluble in organic solvents such as chloroform and m‐cresol and were thermally stable, and PAzMC1 exhibited a high glass transition temperature value (287 °C), while that for PAzMC2 was not observed. UV–visible spectrophotometry revealed absorption bands related to the aromatic backbone of both PAzMCs, 300–285 nm in tetrahydrofuran and 310–301 nm in dimethylsulfoxide, and bands attributed to the conjugated imine unit at around 350 nm. In order to investigate the phenomenon of the emission of fluorescence promoted by dopant agents with regard to potential optoelectronic applications, the materials were doped with H2SO4 and their optical and electrochemical properties investigated. Thus, the absorption band of the imine group was suppressed due to the nitrogen atoms being protonated. Fluorescence spectroscopy analysis developed in dilute solutions of polymers showed no emission from the undoped polymers, whereas the acid‐doped species emitted fluorescence in the UV and violet regions (322 nm). Cyclic voltammetry measurements were carried out and HOMO–LUMO energies were estimated. This study provides a starting point for the development of new poly(azomethine)s with doping‐dependent emission. © 2019 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 99%

New cardo silylated poly(azomethine)s containing 9,9′‐diphenylfluorene units as materials with Brønsted acid‐dependent fluorescence

Hauyon

Garrido‐Gatica

Sobarzo

et al. 2019

Polymer International

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“…These derivatives can be electrochemically oxidized (Yeh et al, 2016). The collective properties (reversible color change with applied potential) have proven ideal for use as electrochromic materials (Ma et al, 2016). While various azomethines have been studied for understating the impact of structure on the absorption and electrochemical properties (Liu et al, 2018), modifying the terminal amine has remained relatively underexplored.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of diethyl 2-amino-5-{4-[bis(4-methylphenyl)amino]benzamido}thiophene-3,4-dicarboxylate

2019

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In the title compound, C31H31N3O5S, the regioselective substitution of the thiophene is confirmed with the amine and the amide at the 2- and 5-positions, respectively. In the molecule, the thiophene ring is twisted by 12.82 (3)° with respect to the aromatic ring of the benzamido group. Intramolecular N—H...O hydrogen bonds are present involving the N atoms of the primary amine and the amide groups, forming S(6) ring motifs. In the crystal, centrosymmetrically related molecules are linked by pairs of N—H...O hydrogen bonds involving the amide carbonyl O atoms and the primary amine N atoms to form dimers of R 2 2(16) ring motif.

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“…Among conjugated polymers, polymeric Schiff bases (polySBs) containing imine bonds (C=N) have been investigated as optoelectronic and electrochemical materials, liquid crystals and metal-catalyst supports among others [ 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. Conjugated polySBs are usually synthesized from aromatic diamines and dialdehyde compounds by polycondensation reactions for obtaining aromatic π-systems in the backbone.…”

Section: Introductionmentioning

confidence: 99%

“…Small molecules and polymers bearing triphenylamine (TPA) moieties have been extensively investigated due to their strong electron-donating and hole transporting/injecting ferromagnetic properties [ 7 , 13 ]. TPA-based compounds are used as building blocks for constructing electrochromic materials such as PLEDs, PSCs and electrochromic (ECs) devices due to their absorption/emission, redox activity, charge transport and ferromagnetism properties [ 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

New Triphenylamine-Based Oligomeric Schiff Bases Containing Tetraphenylsilane Moieties in the Backbone

et al. 2019

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Three new triphenylamine-based oligomeric Schiff bases (polySB1, polySB2 and polySB3) containing tetraphenylsilane core (TPS-core) in the main chain were obtained from TPS-core-based diamines and bis(4-formylphenyl)phenylamine by a high-temperature polycondensation reaction. These new oligomers were structurally characterized by FT-IR, NMR and elemental analysis. All polySBs were highly soluble in common organic solvents, such as chloroform, tetrahydrofuran and chlorobenzene. Samples showed moderate molecular average molecular weight (Mw) and a high thermal stability above 410 °C. Likewise, polySBs showed absorption near 400 nm in the UV-vis range and photoluminescence. The HOMO levels and band-gap values were found in the ranges of −6.06 to −6.18 eV and 2.65–2.72 eV, respectively. The lowest band-gap value was observed for polySB2, which could be attributed to a more effective π-conjugation across the main chain. The results suggest that silicon-containing polySBs are promising wide-band-gap semiconductors materials for optoelectronic applications.

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Immobilized polyazomethines containing triphenylamine groups on ITO: synthesis and acidochromic, electrochemical, electrochromic and photoelectronic properties

Abstract: A new series of polyazomethines (PAMs) containing triphenylamine (TPA) as easily-oxidized units were synthesized as highly soluble materials with electrochromism.

Cited by 34 publications

References 52 publications

New cardo silylated poly(azomethine)s containing 9,9′‐diphenylfluorene units as materials with Brønsted acid‐dependent fluorescence

New cardo silylated poly(azomethine)s containing 9,9′‐diphenylfluorene units as materials with Brønsted acid‐dependent fluorescence

Crystal structure of diethyl 2-amino-5-{4-[bis(4-methylphenyl)amino]benzamido}thiophene-3,4-dicarboxylate

New Triphenylamine-Based Oligomeric Schiff Bases Containing Tetraphenylsilane Moieties in the Backbone

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