New Second-Order NLO Chromophores Based on 3,3‘-Bipyridine: Tuning of Liquid Crystal and NLO Properties

ABSTRACTThe objective of this investigation was to develop stable nonlinear optical (NLO) Materials which possess both second and third order NLO properties. These Materials were envisioned as having a polydiacetylene (PDA) backbone with a second order active NLO chromophoric substituent consisting of a donor group, a π-conjugated bridge, and an acceptor group. The choice of a PDA backbone in this investigation was twofold. In terms of third order NLO properties, the extensive π-conjugation of the PDA backbone leads to large ultrafast third order effects. In terms of second order NLO properties, the high thermal stability and rigidity of the PDA Matrix in a perfect polymeric single crystal is expected to prevent the randomization of the NLO chromophores in the noncentrosymmetric environment. This paper focuses on the synthesis and NLO properties of the unsymmetrical diacetylene Monomers, ((9-Butoxy carbonyl) Methyl urethanyl) -l- (4-urethanyl-4'-nitrobiphenyl) -nona-2,4-diyne, and ((9-Butoxy carbonyl) Methyl urethanyl) -l- (4-urethanyl-4'-nitroazobenzene) -nona-2,4-diyne. The high entropy flexible urethanyl side group was chosen to satisfy the monomer packing requirements for polymerization and enhance the solubility of the PDAs.

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Novel highly conjugated push–pull 4,5-diazafluoren-9-ylidene based efficient NLO chromophores as a springboard for coordination complexes with large second-order NLO properties

Journal of Materials Chemistry ◽

10.1039/c2jm33509c ◽

2012 ◽

Vol 22 (37) ◽

pp. 19761 ◽

Cited By ~ 5

Author(s):

Alessia Colombo ◽

Claudia Dragonetti ◽

Stefania Righetto ◽

Dominique Roberto ◽

Adriana Valore ◽

...

Keyword(s):

Coordination Complexes ◽

Second Order ◽

Nlo Properties ◽

Nlo Chromophores

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Cyclometalated Ir(III) Complexes with Curcuminoid Ligands as Active Second-Order NLO Chromophores and Building Blocks for SHG Polymeric Films

Inorganics ◽

10.3390/inorganics8050036 ◽

2020 ◽

Vol 8 (5) ◽

pp. 36

Author(s):

Mattia Fontani ◽

Alessia Colombo ◽

Claudia Dragonetti ◽

Stefania Righetto ◽

Dominique Roberto ◽

...

Keyword(s):

Electric Field ◽

Second Harmonic ◽

Organic Matrix ◽

Building Blocks ◽

Second Order ◽

Polymeric Films ◽

Ancillary Ligand ◽

Nlo Properties ◽

Nlo Response ◽

Nlo Chromophores

The second-order nonlinear optical (NLO) properties of iridium(III) complexes having two cyclometalated 2-phenylpyridines and curcumin or tetrahydrocurcumin as ancillary ligand have been investigated both in solution and as guest in a polymeric organic matrix. In solution, these complexes are characterized by a significant second-order NLO response, as determined by the Electric Field Induced Second Harmonic (EFISH) technique, like the related complex with acetylacetonate. Whereas the low second-harmonic generation response of a composite film of [Ir(2-phenylpyridine)2(acetylacetonate)] in polymethyl methacrylate was not stable and fell down to zero upon turning off the electric field. A good and stable response was obtained with a film based on the iridium(III) complex bearing two cyclometalated 2-phenylpyridines and curcumin.

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Synthesis and properties of a new second-order NLO chromophore containing the benzo[b]furan moiety for electro-optical materials

RSC Advances ◽

10.1039/c4ra04466e ◽

2014 ◽

Vol 4 (63) ◽

pp. 33312-33318 ◽

Cited By ~ 11

Author(s):

Maolin Zhang ◽

Guowei Deng ◽

Airui Zhang ◽

Huajun Xu ◽

Heyan Huang ◽

...

Keyword(s):

Electron Donor ◽

Optical Materials ◽

Furan Ring ◽

Second Order ◽

Donor Group ◽

Nlo Chromophores ◽

Furan Moiety

We have designed and synthesized a new chromophore having a 1,1,7,7-tetramethyljulolidine fused furan ring as the electron donor group to systematically investigate the role of the benzo[b]furan ring in NLO chromophores.

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A Molecular Architectural Approach to Second-Order Nonlinear Optical Materials

MRS Proceedings ◽

10.1557/proc-392-27 ◽

1995 ◽

Vol 392 ◽

Cited By ~ 2

Author(s):

Xiaoguang Yang ◽

Duncan McBranch ◽

Basil Swanson ◽

Dequan Li

Keyword(s):

Nonlinear Optical ◽

Second Harmonic ◽

Fused Silica ◽

Second Order ◽

Nonlinear Susceptibility ◽

Design And Synthesis ◽

Fundamental Wavelength ◽

Assembled Monolayers ◽

Methylene Groups ◽

Nlo Chromophores

AbstractThe design and synthesis of a family of calix[4]arene-based nonlinear optical (NLO) chromophores are discussed. The calixarene chromophores are macrocyclic compounds consisting of four simple D-π-A units bridged by methylene groups. These molecules were synthesized such that four D-π-A units of the calix[4]arene were aligned along the same direction with the calixarene in a cone conformation. These nonlinear optical super-chromophores were subsequently fabricated into covalently bound self-assembled monolayers on the surfaces of fused silica and silicon. Spectroscopic second harmonic generation (SHG) measurements were carried out to determine the absolute value of the dominant element of the second-order nonlinear susceptibility, d33, and the average molecular alignment, ψ. We find a value of d33 = 60 pm/V at a fundamental wavelength of 890 nm, and ψ˜ 36° with respect to the surface normal.

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Novel glass-forming ferroelectric liquid-crystal material of high second-order nonlinearity

Applied Physics B ◽

10.1007/bf01081178 ◽

1994 ◽

Vol 59 (6) ◽

pp. 591-595 ◽

Cited By ~ 11

Author(s):

M. Loddoch ◽

G. Marowsky ◽

H. Schmid ◽

G. Heppke

Keyword(s):

Liquid Crystal ◽

Second Order ◽

Ferroelectric Liquid Crystal ◽

Glass Forming ◽

Crystal Material ◽

Liquid Crystal Material ◽

Second Order Nonlinearity

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Synthesis and characterization of novel second-order NLO-chromophores bearing pyrrole as an electron donor group

Tetrahedron ◽

10.1016/j.tet.2012.07.082 ◽

2012 ◽

Vol 68 (39) ◽

pp. 8147-8155 ◽

Cited By ~ 26

Author(s):

M. Cidália R. Castro ◽

M. Belsley ◽

A. Maurício C. Fonseca ◽

M. Manuela M. Raposo

Keyword(s):

Electron Donor ◽

Second Order ◽

Synthesis And Characterization ◽

Donor Group ◽

Nlo Chromophores

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THE INVESTIGATION OF ELECTRONIC PROPERTIES AND MICROSCOPIC SECOND-ORDER NONLINEAR OPTICAL BEHAVIOR OF 1-SALICYLIDENE-3-THIO-SEMICARBAZONE

Journal of Nonlinear Optical Physics & Materials ◽

10.1142/s0218863507003573 ◽

2007 ◽

Vol 16 (01) ◽

pp. 91-99 ◽

Cited By ~ 15

Author(s):

ASLI KARAKAS ◽

HUSEYIN UNVER ◽

AYHAN ELMALI

Keyword(s):

Molecular Orbital ◽

Electronic Transition ◽

Nonlinear Optical ◽

Dipole Moments ◽

Empirical Method ◽

Second Order ◽

Nlo Properties ◽

Calculation Results ◽

Moller Plesset ◽

Semi Empirical

To investigate the microscopic second-order nonlinear optical (NLO) behavior of the 1-salicylidene-3-thio-semicarbazone Schiff base compound, the electric dipole moments (μ), linear static polarizabilities (α) and first static hyperpolarizabilites (β) have been calculated using finite field second-order Møller-Plesset perturbation (FF MP2) theory. The ab-initio results on (hyper)polarizabilities show that the investigated molecule might have microscopic NLO properties with non-zero values. To understand the NLO behavior in the context of molecular orbital structure, we have also examined the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and the HOMO-LUMO gap in the same theoretical framework as the (hyper)polarizability calculations. In addition to the NLO properties, the electronic transition spectra have been computed using a semi-empirical method (ZINDO). ZINDO calculation results show that the electronic transition wavelengths have been estimated to be shorter than 400 nm.

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