Synthesis, crystal structures, and quadratic nonlinear optical properties in a series of push–pull boronate derivatives

Reyes, Horacio; Muñoz, Blanca M.; Farfán, Norberto; Santillán, Rosa; Rojas‐Lima, Susana; Lacroix, Pascal G.; Nakatani, Keitaro

doi:10.1039/b205308j

Cited by 49 publications

(42 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The research in the field of organic NLO materials has gained momentum in the recent past on account of their interesting nonlinear optical effects extended to optical parametric amplifiers, optical parametric oscillators, Qswitched optical applications, etc [1][2][3][4][5]. However, most of the organic NLO crystals are associated with poor mechanical strength and thermal stability [6,7].…”

Section: Introductionmentioning

confidence: 98%

Synthesis, crystal growth and properties of the charge transfer complex adduct of 2‐nitro aniline with picric acid – An organic non‐linear optical material

Bharathikannan

Chandramohan

Kandhaswamy

et al. 2008

Cryst. Res. Technol.

View full text Add to dashboard Cite

The organic NLO material 2-nitro aniline and picric acid (2NAP) was synthesized, needle shaped single crystals of dimension 10 × 1 × 0.8 mm 3 were grown by slow evaporation solution growth technique from the saturated solution of the title compound in chloroform at ambient temperature. The material was characterized through elemental analysis, powder XRD, 1 H NMR, 13 C NMR and FTIR techniques. The various planes of reflection have been identified from the XRD powder pattern. The formation of the charge transfer complex was confirmed by UV-VIS spectroscopy. The thermal stability of the crystals was investigated using TG/DTA analyses techniques. The second harmonic generation (SHG) efficiency of the material was estimated using Nd: YAG laser as source.

show abstract

Section: Introductionmentioning

confidence: 98%

Synthesis, crystal growth and properties of the charge transfer complex adduct of 2‐nitro aniline with picric acid – An organic non‐linear optical material

Bharathikannan

Chandramohan

Kandhaswamy

et al. 2008

Cryst. Res. Technol.

View full text Add to dashboard Cite

show abstract

“…The initial motivation in this study came from the previous observation that the 1 H NMR shift of the hydrogen of the imine function ( HC N ) was strongly dependent on the nature of the substituted Ar-B fragment, thus providing a way to tune the electronic features of the bridge and hence, the NLO response. However, and due to the bent structure of the skeleton, the NLO response of 16 is significantly lower than that of the related stilbazole parents with ˇ values in the 25-30 × 10 −30 esu range for 16a, and 45-50 × 10 −30 esu range, whatever the nature of R 1 -R 5 [32]. This approach was later applied in a series of related tin-based chromophores [35].…”

Section: Schiff-bases Complexes Of Boron and Tinmentioning

confidence: 90%

“…Furthermore, a computational investigation suggests that the rotation of the aryl around the C B bond can Table 1 Experimental ˇ values for 16 and 17 recorded by EFISH (see ref [32] and [35] lead to a short R 5 -O contact (dotted R 5 -O line in Chart 2), thus providing a route for a possible modulation of the charge transfer and, eventually of the ˇ value. From the latter observation, the issue of inducing the switching of NLO properties by conformational changes arises naturally.…”

Section: Schiff-bases Complexes Of Boron and Tinmentioning

confidence: 99%

“…The investigation of the NLO properties of the molecules 11-15 (Chart 2) reported previously was part of an important collaboration initiated 15 years ago with a group of chemists of Mexico, wishing to renew their scientific collaborations outside the American sphere, in the perspective of finding applications of organo-boron [32][33][34] and tin [35][36][37] derivatives in optics. Altogether, there were only few boron and tin based NLO molecules reported in the literature.…”

Section: Schiff-bases Complexes Of Boron and Tinmentioning

confidence: 99%

See 1 more Smart Citation

Second-order nonlinear optics in coordination chemistry: An open door towards multi-functional materials and molecular switches

Lacroix

Malfant

Lepetit

2016

Coordination Chemistry Reviews

Self Cite

View full text Add to dashboard Cite

“…Espera-se que essa característica ímpar dote os compostos organoboranos trivalentes de boas ou ótimas propriedades óticas não-lineares. De fato, Reyes et al 8 estudaram a eficiência da geração de segundo harmônico (SHG) por amostras sólidas (pó) de boranos tetravalentes imino fenólicos do ácido salicílico, e, nesses experimentos, não foram observados sinais SHG para moléculas contendo grupos doadores de elétrons fortes como dietilamina. Somente os derivados metoxi exibiram uma modesta eficiência na geração de um segundo harmônico (SHG).…”

Section: Introductionunclassified

Polarizabilidades e primeira hiperpolarizabilidades elétricas dipolares de ésteres E-4-amino-trans-1,3-butadienil-(1',2'-di-hidroxibenzeno) de boro, alumínio e gálio

Procópio¹,

Cesar²

2009

Quím. Nova

View full text Add to dashboard Cite

Recebido em 7/5/08; aceito em 12/1/09; publicado na web em 28/5/09 DIPOLE POLARIZABILITIES AND FIRST HYPERPOLARIZABILITIES OF E-4-AMINE-TRANS-1,3-BUTADIENYL-(1′,2′-DIHYDROXIBENZENE) ESTERS OF BORON, ALUMINUM AND GALLIUM.Static electric dipole polarizabilities and first hyperpolarizabilites have been calculated for the title molecules and their 3′ and 4′-nitro derivatives at ab-initio Hartree-Fock/6-31G(d,p) level. The influence of the pivotal p vacant 3A elements (B, Al or Ga) substitution on the electrical properties of these molecules is detailed. The axial vector components of the first hyperpolarizabilities β(0) of the push-pull 4′−nitro derivatives, −18.2×10 −32 esu (B), −21.1×10 −32 esu (Al) and −20.8×10 −32 esu (Ga) are calculated to be as much as fourfold larger then that calculated for the p-nitroaniline, a reference organic molecule for comparison for this type of molecular property.Keywords: dipole (hyper)polarizabilities; boronates, aluminates and galiates; Hartree-Fock calculations. INTRODUÇÃOMoléculas orgânicas insaturadas contendo um sistema de elétrons conjugados, localizados em unidades individuais ou estendidas na forma de cadeias poliméricas, formam uma grande classe de materiais que apresentam ótimas características óticas não-lineares. [1][2][3][4] A combinação desses sistemas orgânicos com centros metálicos adequados produz, complementarmente, importantes exemplos de derivados organometálicos que desenvolvem valores promissores para os parâmetros que descrevem essas propriedades óticas. 5As respostas óticas não-lineares de compostos moleculares originam-se, microscopicamente, nas excitações virtuais que seus elétrons podem sofrer ao se moverem de orbitais ocupados para orbitais não ocupados, em especial, entre os orbitais de valência de menores energias HOMO e LUMO. A facilidade com que essas excitações ocorrem está diretamente relacionada com a capacidade da radiação eletromagnética em interagir com um sistema molecular e, assim, induzir consideráveis transferências de cargas entre o estado eletrônico fundamental e os estados eletrônicos excitados de baixa energia. Essa polarização de cargas favorece o surgimento de polarizabilidades α(0) e hiperpolarizabilidades elétricas (β(0) (primeira), γ(0) (segunda) etc.) apropriadas para o desenvolvimento de materiais com propriedades óticas não lineares.1,2 A união de grupos doadores (D) e retiradores (R) eficientes de elétrons, intercalados por um sistema de elétrons π-conjugados como, por exemplo, o grupo aromático fenila ou a cadeia aberta do trans-1,3-butadienila, formam um conjunto de moléculas (chamados sistemas eletrônicos do tipo push-pull D-R) que apresentam excelentes hiperpolarizabilidades elétricas moleculares. A escolha da combinação adequada do par D e R e a presença de um intercalador insaturado, que atua como caminho para deslocalização dos elétrons é fundamental na construção de moléculas que apresentam maiores parâmetros óticos não-lineares. Usualmente, os grupos amino −NH 2 , e nitro −NO 2 são os mais utilizados como unidades doa...

show abstract

Synthesis, crystal structures, and quadratic nonlinear optical properties in a series of push–pull boronate derivatives

Cited by 49 publications

References 46 publications

Synthesis, crystal growth and properties of the charge transfer complex adduct of 2‐nitro aniline with picric acid – An organic non‐linear optical material

Synthesis, crystal growth and properties of the charge transfer complex adduct of 2‐nitro aniline with picric acid – An organic non‐linear optical material

Second-order nonlinear optics in coordination chemistry: An open door towards multi-functional materials and molecular switches

Polarizabilidades e primeira hiperpolarizabilidades elétricas dipolares de ésteres E-4-amino-trans-1,3-butadienil-(1',2'-di-hidroxibenzeno) de boro, alumínio e gálio

Contact Info

Product

Resources

About