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Abstract

The opto(electrical) properties and theoretical calculations of polyazomethine with vinylene and phenantridine moieties in the main chain were investigated in the present study. 2,5-Bis(hexyloxy)-1,4-bis[(2,5-bis(hexyloxy)-4-formyl-phenylenevinylene]benzene was polymerized in solution with 3,8-diamino-6-phenylphenanthridine (PAZ-PV-Ph). The temperatures of 5% weight loss (T _5%) of the polyazomethine was observed at 356 °C in nitrogen. Electrochemical properties of thin film of the polymer were studied by differential pulse voltammetry. The HOMO level of the PAZ-PV-Ph was at −4.97 eV. The energy band gap (E _g) was detected of approximately ∼1.9 eV. Energy band gap (E _gopt) was additionally calculated from absorption spectrum and absorption coefficient α. The absorption UV-vis spectra of polyazomethine recorded in solution showed a blue shift in comparison with the solid state. HOMO-LUMO levels and E _g were additionally calculated theoretically by density functional theory and molecular simulations of PAZ-PV-Ph are presented. Current density–voltage (J–U) measurements were performed on ITO/PAZ-PV-Ph/Al, ITO/TiO2/PAZ-PV-Ph/Al and ITO/PEDOT/PAZ-PV-Ph:TiO2/Al devices in the dark and during irradiation with light (under illumination of 1000 W m⁻²). The polymer was tested using AFM technique and roughness (R _a, R _ms) along with skew and kurtosis are presented.

Keywords

polyazomethines current density–voltage characteristics HOMO-LUMO theoretical calculations

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References

Iwan

Sek

. Processible polyazomethines and polyketanils: From aerospace to light emitting diodes and other advanced applications. Prog Polym Sci 2008; 33: 289–345.

Niu

Huang

Bai

. Study on crystallization, thermal stability and hole transport properties of conjugated polyazomethine materials containing 4,4'-bisamine-triphenylamine. Mater Chem Phys 2004; 86: 33–37.

Niu

H-J

Huang

Y-D

Bai

X-D

. Novel poly-Schiff bases containing 4,4'-diamino-triphenylamine as hole transport material for organic electronic device. Mater Lett 2004; 58: 2979–2983.

Sek

Jarzabek

Grabiec

. A study of thermal, optical and electrical properties of new branched triphenylamine-based polyazomethines. Synth Met 2010; 160: 206–2076.

Sek

Iwan

Kaczmarczyk

. Supramolecular modification of optical properties of some new polyazomethines. Mol Cyst Liq Cryst 2007; 468: 119–129.

Sek

Iwan

Jarzabek

. Hole transport triphenylamine-azomethine conjugated system: Synthesis and optical, photoluminescence and electrochemical properties. Macromolecules 2008; 41: 6653–6663.

Sek

Iwan

Jarzabek

. Characterization and optical properties of oligoazomethines with triphenylamine moieties exhibiting blue, blue-green and green light. Spectrochim Acta Part A: Mol Biomol Spectrosc 2009; 72: 1–10.

Liou

G-S

Lin

H-Y

Hsieh

Y-L

. Synthesis and characterization of wholly aromatic poly(azomethine)s containing donor--acceptor triphenylamine moieties. J Polym Sci Part A. Polym Chem 2007; 45: 4921–4932.

Hindson

Ulgut

Friend

. All-aromatic liquid crystal triphenylamine-based poly(azomethine)s as hole transport materials for opto-electronic applications. J Mater Chem 2010; 20: 937–944.

10.

Iwan

Palewicz

Sikora

. Aliphatic-aromatic poly(azomethine)s with ester groups as thermotropic materials for opto(electronic) applications. Synth Met 2010; 160: 1856–1867.

11.

Iwan

Schab-Balcerzak

Pociecha

. Characterization, liquid crystalline behavior, electrochemical and optoelectrical properties of new poly(azomethine)s and poly(imide) with siloxane linkages. Opt Mater 2011; 34: 61–74.

12.

Rohlfing

Bradley

DDC

. Non-linear Stark effect in polyazomethine and poly(p-phenylene-vinylene): the interconnection of chemical and electronic structure. Chem Phys 1998; 227: 133–151.

13.

Iwan

Mazurak

Kaczmarczyk

. Synthesis and characterization of polyketanils with 3,8-diamino-6-phenylphenanthridine moieties exhibiting light emitting properties. Molecular and supramolecular engineering concept. Spectrochim Acta Part A: Molec Biomolec Spectr 2008; 69: 291–303.

14.

Iwan

Kaczmarczyk

Jarzabek

. Influence of long-chain aliphatic dopants on the spectroscopic properties of polyketimine containing 3,8-diamino-6-phenylphenanthridine and ethylene linkage in the main chain. Noncovalent interaction: Proton transfer, hydrogen and halogen bonding. Phys Chem A 2008; 112: 7556–7566.

15.

Cimecioglut

Weiss

. Aromatic polyamides of 3,8-diamino-6-phenylphenanthridina end their molecular complexes with sulfonated polystyrene ionomers. Macromolecules 1995; 28: 6343–6346.

16.

Becke

. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993; 98: 5648–5652.

17.

Frisch

Trucks

Schlegel

. Gaussian 03, Revision E1, Wallingford CT: Gaussian, Inc., 2004.

18.

Sek

Kaczmarczyk

Jarzabek

. Nowe fotoluminescencyjne poliazometiny. Modyfikacja polimerow. Stan i perspektywy w roku 2007. Wroclaw, Poland: Wydział Chemiczny Politechniki Wrocławskiej, 2007, pp. 307–310.

19.

Yang

Jenekhe

. Conjugated aromatic polyimines. 2. Synthesis, structure and properties of new aromatic polyazomethines. Macromolecules 1995; 28: 1180–1196.

20.

Rusu

Airinei

Rusu

. On the electronic transport mechanism in thin films of some new poly(azomethine sulfone)s. Acta Materialia 2007; 55: 433–442.

21.

Jarzabek

Weszka

Burian

. Optical properties of amorphous thin films of the Zn-P system. Thin Solid Films 1996; 279: 204–208.

22.

Gierschner

Cornil

Egelhaaf

H-J

. Optical band gaps of p-conjugated organic materials at the polymer limit: Experiment and theory. Adv Mater 2007; 19: 173–191.

23.

Masui

Ohmori

. Anodic oxidation of Schiff bases. Part I. Oxidation of N-benzylidene-p-anisidines in acetonitrile. J Chem Soc Perkin Trans 1972; 2: 1882–1887.

24.

Cao

Gao

. Electrochemical properties of luminescent polymers and polymer light-emitting electrochemical cells. Synth Met 1999; 99: 243–248.

25.

Pommerehne

Vestbeber

Guss

. Efficient two layer leds on a polymer blend basis. Adv Mater 1995; 7: 551–554.

26.

Root

Smith

. Electrochemical behavior of selected imine derivatives, reductive carboxylation, alpha-amino acid synthesis. J Electrochem Soc 1982; 129: 1231–1236.

27.

Freire

Neves

CMSS

Marrucho

. Hydrolysis of tetrafluoroborate and hexafluorophosphate counter ions in imidazolium-based ionic liquids. J Phys Chem A 2010; 114: 3744–3749.

28.

Gebala

Jones

. A rate study of the hydrolysis of the hydroxypentafluoroarsenate(V) anion. J Inorg Nucl Chem 1969; 31: 771–776.

29.

Lupton

. Single-molecule spectroscopy for plastic electronics: materials analysis from the bottom-up. Adv Mater 2010; 22: 1689–1721.

30.

Becker

Da Como

Feldmann

. How chromophore shape determines the spectroscopy of phenylene–vinylenes: Origin of spectral broadening in the absence of aggregation. J Phys Chem B Lett 2008; 112: 4859–4864.

31.

Kemerink

van Duren

JKJ

Jonkheijm

. Relating substitution to single-chain conformation and aggregation in poly(p-phenylene vinylene) films. Nano Lett 2003; 3: 1191–1196.

32.

Wijsboom

Sheynin

Patra

. Tuning of electronic properties and rigidity in PEDOT analogs. J Mater Chem 2011; 21: 1368–1372.

33.

Hreniak

Nyk

Hreniak

. Optical property, nanocrystalline films, synthesis of europium. Materials Science-Poland 2004; 22: 227–234.

34.

Mukherjee

Karthik

Ravishankar

. Hybrid sol–gel combustion synthesis of nanoporous anatase. J Phys Chem C 2009; 113: 18204–18211.

35.

Nolan

Seery

Pillai

. Spectroscopic investigation of the anatase-to-rutile transformation of sol–gel-synthesized TiO2 photocatalysts. J Phys Chem C 2009; 113: 16151–16157.

36.

Yan

Mahurin

Overbury

. Nonhydrolytic layer-by-layer surface sol–gel modification of powdered mesoporous silica materials with TiO₂ . Chem Mater 2005; 17: 1923–1925.

Polyazomethine with vinylene and phenantridine moieties in the main chain: Synthesis,characterization,opto(electrical) properties and theoretical calculations

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