Polyazomethine conjugated polymer film with second order nonlinear optical properties fabricated by electric-field-assisted chemical vapor deposition

Tatsuura, Satoshi; Sotoyama, Wataru; Motoyoshi, Katsusada; Matsuura, Akira; Hayano, Tomoaki; Yoshimura, Tetsuzo

doi:10.1063/1.109462

Cited by 13 publications

(9 citation statements)

References 5 publications

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“…Electric fields applied either parallel or perpendicular to the substrate surface during growth in UHV has also been demonstrated to be useful in manipulation of structure. These techniques have been applied to both small molecular weight polar and nonpolar OMCs, and polymers − as a means to orient dipolar molecules with large nonlinear optical coefficients. The applied fields are a means for in situ molecular poling, similar to methods used to align electrooptic chromophores in polymers heated above their glass transition temperature .…”

Section: 0 the Future Of Ordered Organic Thin Films Grown In The Vapo...mentioning

confidence: 99%

“…The applied fields are a means for in situ molecular poling, similar to methods used to align electrooptic chromophores in polymers heated above their glass transition temperature. 14 For this purpose, orienting the field in-plane using closely spaced electrodes pre-patterned on the substrate prior to growth [419][420][421]423,424 can be more effective in generating high fields which are sufficient(>10 5 V/cm) to induce molecular ordering, than using fields oriented perpendicular to the substrate using external field apparatus such as grids, 418,422 where comparatively small fields (∼10 4 V/cm) are possible.…”

Section: Limitations Of Ombdmentioning

confidence: 99%

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Ultrathin Organic Films Grown by Organic Molecular Beam Deposition and Related Techniques

1997

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Section: 0 the Future Of Ordered Organic Thin Films Grown In The Vapo...mentioning

confidence: 99%

Section: Limitations Of Ombdmentioning

confidence: 99%

Ultrathin Organic Films Grown by Organic Molecular Beam Deposition and Related Techniques

1997

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“…Polyazomethines, or poly(1,4-phenylenemethylidynenitrilo-1,4-phenylenenitrilomethylidyne) (PPI), have been widely explored as potential nonlinear optical materials, with derivatives prepared via polycondensation of diamine and dialdehyde monomers in solution or by chemical vapor deposition. − Recently, soluble polyazomethines have been shown to work in bulk heterojunction organic solar cells . The facile low-temperature polycondensation reaction to form PPI and its derivatives makes it attractive relative to other polymers in organic electronics by virtue of its simplicity and lack of side reactions.…”

Section: Introductionmentioning

confidence: 99%

Doping-Induced Immobile Charge Carriers in Polyazomethine: A Spectroscopic Study

et al. 2013

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Herein, we report the effect of protonation on the electronic properties and the conductivity of a soluble derivative of polyazomethine, poly(1,4-(2,5-bisoctyloxy phenylenemethylidynenitrilo)-1,4-phenylenenitrilomethylidyne), BOO-PPI. Following protonation, a marked change in electronic structure occurs, as evidenced by a bathochromic shift in visible absorption and the appearance of a broad absorption in the infrared coupled with new infrared active vibrational modes, signaling the appearance of a new electronic state. In other conjugated polymers, such features usually evidence the formation of mobile polarons on the polymer chain, leading to an increase in electrical conductivity. Surprisingly, BOO-PPI protonation does not lead to such an increase. Protonation also does not result in an electron spin resonance signal. We propose a model for protonation inducing a charged state on the polymer chain with strongly limited delocalization accounting for the lack of the electron spin resonance signal and the missing conductivity. To our knowledge, this is the first time that spectral features usually corresponding to mobile charges in organic materials do not correspond to an actual change in conductivity.

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“…3 We are particularly interested in conjugated poly(azomethine)s due to their documented excellent thermal, mechanical, electronic, optical, optoelectronic, and fiberforming properties. [4][5][6][7][8][9][10][11][12][13][14][15][16] The general chemical structure of conjugated poly(azomethine)s is [-(Ar 1 )-CHdN-(Ar 2 )-NdCH-] n . The CdN linkages of poly(1,4-phenylenemethylidyneitrilo-1,4-phenylenenitrilomethylidyne) (PPI) are isoelectronic with the CdC linkages of poly(p-phenylene vinlyene) (PPV) and result in a significant difference in the electronic and optoelectronic properties.…”

Section: Introductionmentioning

confidence: 99%

New Thiophene-Linked Conjugated Poly(azomethine)s: Theoretical Electronic Structure, Synthesis, and Properties

et al. 2005

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We report a joint theoretical and experimental study of several new thiophene-based poly(azomethine)s. Hybrid density functional theory (DFT) method was used to calculate the optimized geometry and electronic structure of poly(azomethine)s. Theoretical band gaps of the new thiophene-based poly(azomethine)s were in the range 2.33−2.67 eV, which are smaller than that of the phenylene-based polymer. The variation of the backbone ring (fluorene, carbazole, or naphthalene) or donor/acceptor side group on the phenylene ring significantly affected the dihedral angles and resulted in the variation of electronic properties (ionization potential, electron affinity, and band gap) of the poly(azomethine)s. Five soluble new conjugated poly(azomethine)s derived from the polymerization of 2,5-diformyl-3-hexylthiophene (DFHT) with various diamines were prepared and characterized. The optical and electrochemical band gaps of the polymer films were in the ranges 2.21−2.28 and 2.13−2.24 eV, respectively. The trend of the effect of the backbone ring or side chain on the experimental electronic properties is in good agreement with the theoretical results. Our study demonstrates how the electronic properties of conjugated poly(azomethine)s can be tuned by the backbone ring or side group, which could be important for electronic or optoelectronic applications of the materials.

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Polyazomethine conjugated polymer film with second order nonlinear optical properties fabricated by electric-field-assisted chemical vapor deposition

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Cited by 13 publications

References 5 publications

Ultrathin Organic Films Grown by Organic Molecular Beam Deposition and Related Techniques

Ultrathin Organic Films Grown by Organic Molecular Beam Deposition and Related Techniques

Doping-Induced Immobile Charge Carriers in Polyazomethine: A Spectroscopic Study

New Thiophene-Linked Conjugated Poly(azomethine)s: Theoretical Electronic Structure, Synthesis, and Properties

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