Theoretical assessment of the nonlinear optical properties of substituted oligoacenes

Costa, Marconi B. S.; Machado, Ana E. de A.; Pavão, Antonio C.

doi:10.1007/s10853-012-6728-0

Cited by 6 publications

(10 citation statements)

References 18 publications

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“…L, E, and P are the leucoemeraldine, emeraldine and pernigraniline forms respectively,  0 ( 0 ) is the static value,  1060 ( 2479 ) is the dynamic value at the 1060 nm (2479 nm),  is the ground state dipole moment,  H-L is the HOMO-LUMO energy gap, and the IP is the ionization potential. It was found that the halogenated hexamers of aniline present high values of , in agreement with previous studies (Costa et al, 2007(Costa et al, , 2012Machado et al, 2004;Machado et al, 2011a). For leucoemeraldine hexamers the higher values of  are associated with the smaller values of  H-L ( Figure 3a).…”

Section: Resultssupporting

confidence: 91%

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Nonlinear Optical Properties of Halogenated Aniline Oligomers

Costa¹,

Pavão

Machado³

2013

JMSR

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High values of the first (b) and second (g) hyperpolarizabilities were obtained for the halogenated oligomers of the three neutral forms of polyaniline (pernigraniline, emeraldine, and leucoemeraldine). For enhancement of the b and g magnitudes, the t-butyl, t-butoxy, and dimethylamine electron donor groups were introduced into various halogenated oligomers. The effect of the oligomer chain size on the b and g magnitude was also investigated by considering the aniline trimers and hexamers. The highest value of the dynamic b hyperpolarizability (1060 nm) for the second-order harmonic generation (SHG) was found for a pernigraniline hexamer containing fluorine and dimethylamine substituents. The highest g hyperpolarizability magnitudes for the third-order harmonic generation (THG) were observed for all halogenated pernigraniline hexamers containing dimethylamine as a substituent. The AM1/TDHF results show that the halogenated aniline-based molecules are promising candidates for applications in nonlinear optics

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Section: Resultssupporting

confidence: 91%

“…This value is of the same magnitude order as the value experimentally observed for polyaniline (Azevêdo et al, 2002). These systems with highest values of  and  present very small  H-L values as observed for other nonlinear organic molecules (Costa et al, 2007(Costa et al, , 2012Machado et al, 2004Machado et al, , 2011a.…”

Section: Resultssupporting

confidence: 82%

Nonlinear Optical Properties of Halogenated Aniline Oligomers

Costa¹,

Pavão

Machado³

2013

JMSR

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“…Furthermore, several oligoanilines and hybrid materials containing aniline moieties show significant first ( β ) and second ( γ ) hyperpolarizabilities, as demonstrated by theoretical studies [17–22] . The introduction of electron‐donating ( D ) and/or electron‐withdrawing ( A ) groups into the structure of an oligomer promotes a marked increase in the β nonlinear response [17,21–29] …”

Section: Introductionmentioning

confidence: 97%

“…[17][18][19][20][21][22] The introduction of electron-donating (D) and/or electron-withdrawing (A) groups into the structure of an oligomer promotes a marked increase in the β nonlinear response. [17,[21][22][23][24][25][26][27][28][29] Multidisciplinary research groups have shown that some parameters, such as the molecular conformation, asymmetry, delocalisation, spin multiplicity and charge transfer (CT) processes, correlate with the nonlinear response of oligomeric derivatives. [17,[21][22][23][24][25][26][28][29][30] The enhanced nonlinear coefficients of second-order optical materials are required for all-optical switching and electro-modulation.…”

Section: Introductionmentioning

confidence: 99%

“…The selected D and A groups contribute to increase the nonlinear response of several organic compounds. [17,21,[23][24][25][26][27]29] Subsequently, the β magnitudes of the nonfunctionalized octamers were computed to accounting for the effect of those substituent groups on the nonlinear coefficient. In a previous study, we demonstrated the influence of oligomer size on the nonlinear response for nonfunctionalized and functionalized aniline tetramers and octamers.…”

Section: Introductionmentioning

confidence: 99%

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Nonlinear Optical and Spectroscopical Properties of Functionalized Oligoanilines

et al. 2021

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Functionalized octamers of polyaniline neutral forms (leucoemeraldine, emeraldine, pernigraniline) were studied in order to optimize the first hyperpolarizabilities (β). Remarkable static β values were found for the pernigraniline and emeraldine derivatives by using the coupled perturbed Kohn-Sham (CPKS) approach at the PBE1PBE/6-31G** level. The enhanced nonlinear response was achieved through the introduction of donor (D) and/or acceptor (A) groups into the oligoanilines structures. The nonlinear optical (NLO) properties of the octamers missing the substituent groups were also investigated. The largest β values were obtained for the pernigraniline and emeraldine derivatives having the tert-butyl (D) and dicyanoethenyl (A) substituents at opposite ends, as well as the ones with only the acceptor group. These oligomers show charge transfer transitions with large oscillator strengths according to the time dependent density functional theory (TD-DFT). Predicted β values for the majority of functionalized oligoanilines strongly indicate them as potential building blocks for molecular-based nonlinear materials with secondorder response.

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Anti‐Stokes Fluorescence and Nonlinear Optical Properties of the Functionalized Phenoxazine‐based Dye: A computational study

Kuniyil

Padmanaban

2021

ChemistrySelect

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Tuning of electronic, photophysical and nonlinear optical (NLO) properties of the phenoxazin‐3‐one dye, resazurin (Rz), is here attempted through functionalization by employing the electron‐donating and electron‐withdrawing groups. Density functional theory (DFT) and time‐dependent DFT calculations were performed for the purpose. Examining the absorption‐emission spectra, featuring an intense band (ππ*) followed by a weak band (nπ*), of the functionalized dye derivatives reveal the Stokes shift, and relatively a large shift is found for the cyano‐functionalized Rz molecules. Surprisingly, the 2‐mono‐cyanoresazurin shows the anti‐Stokes fluorescence (ASF) emission induced by the hot‐band absorption, and at the other end, the weak absorption band associated to the charge transfer nπ* transition of the nitro‐functionalized molecules is being quenched. Radiative lifetime analysis infers that the pull‐type functionalized molecules decay slowly whereas the push‐type shows the high emission rate. The structure‐property relations between the molecular parameters were also discussed. Tuning the NLO properties infers that the pull‐type group exhibits significantly high hyperpolarizabilities (for cyano‐) whereas the push‐type exhibits relatively small β‐value (for amino‐) when compared the standard NLO molecule. Here, the tetra‐functionalized‐Rz molecules may act as promising candidates for NLO applications, and also probing their ASF emission further unfolds the bio‐applications.

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Theoretical assessment of the nonlinear optical properties of substituted oligoacenes

Cited by 6 publications

References 18 publications

Nonlinear Optical Properties of Halogenated Aniline Oligomers

Nonlinear Optical Properties of Halogenated Aniline Oligomers

Nonlinear Optical and Spectroscopical Properties of Functionalized Oligoanilines

Anti‐Stokes Fluorescence and Nonlinear Optical Properties of the Functionalized Phenoxazine‐based Dye: A computational study

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