Solvent effects on static polarizability, static first hyperpolarizability and one- and two-photon absorption properties of functionalized triply twisted Möbius annulenes: a DFT study

Alam, Md. Mehboob; Kundi, Varun; Thankachan, Pompozhi Protasis

doi:10.1039/c6cp02732f

Cited by 15 publications

(17 citation statements)

References 66 publications

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“…This molecule is the first example of a triply twisted Möbius annulene. DFT calculations on the triply twisted annulene 176 and related macrocycles were recently reported from other research groups …”

Section: Angle‐strained Alkyne‐containing π‐Conjugated Macrocyclesmentioning

confidence: 99%

“…DFT calculations on the triply twisted annulene 176 and related macrocycles were recently reported from other research groups. [287][288][289][290] Miki, Ohe, and co-workers recently reported the 2,2'-diethynyl-1,1'-binaphthyl-containing carbon double helices ( Figure 56). [291] The precursor (S,S)-177 wass ynthesized by using macrocyclization under Sonogashira-Hagihara coupling conditions.…”

Section: Thiophene Spacersmentioning

confidence: 99%

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π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

Miki

Ohe

2019

Chemistry A European J

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Angle‐strained alkyne‐containing π‐conjugated macrocycles are attractive compounds both in functional materials chemistry and biochemistry. Their interesting reactivity as well as photophysical and supramolecular properties have been revealed in the past three decades. This review highlights the recent advances in angle‐strained alkyne‐containing π‐conjugated macrocycles, especially their synthetic methods, the bond angles of alkynes (∠sp at C≡C−C), and their functions. The theoretical and experimental research on cyclo[n]carbons and para‐cyclophynes consisting of ethynylenes and para‐phenylenes are mainly summarized. Related macrocycles bearing other linkers, such as ortho‐phenylenes, meta‐phenylenes, heteroaromatics, biphenyls, extended aromatics, are also overviewed. Bond angles of strained alkynes in π‐conjugated macrocycles, which are generable, detectable, and isolable, are summarized at the end of this review.

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Section: Angle‐strained Alkyne‐containing π‐Conjugated Macrocyclesmentioning

confidence: 99%

Section: Thiophene Spacersmentioning

confidence: 99%

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

Miki

Ohe

2019

Chemistry A European J

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“…Several experimental and theoretical works have contributed to these goals. For example, the effect of π−conjugation, [16][17][18] bond-length alternation, [19][20][21] and solvent 22,23 have been explored experimentally and/or theoretically.…”

Section: Introductionmentioning

confidence: 99%

A generalized few-state model for the first hyperpolarizability

Alam

Beerepoot

Ruud

2020

The Journal of Chemical Physics

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The properties of molecules depend on their chemical structure and thus structure-property relations help design molecules with desired properties. Few-state models are often used to interpret experimental observations of nonlinear optical properties. Not only the magnitude, but also the relative orientation of the transition dipole moment vectors is needed for few-state models of the non-linear optical properties. The effect of the relative orientation of the transition dipole moment vectors is called dipole alignment and this effect has previously been studied for multiphoton absorption properties. However, so far no such studies are reported for the first hyperpolarizability. Here we present a generalized few-state model for the static and dynamic first hyperpolarizability β , accounting for the effect of dipole alignment. The formulae derived in this work are general in the sense that they can be used for any few-state model, i.e. two-state model, three-state model or in general an n-state model. Based on the formulae, we formulate minimization and maximization criteria for the alignment of transition dipole moment vectors. We demonstrate the importance of dipole alignment by applying the formulae to the static first hyperpolarizability of ortho-, metaand para-nitroaniline. The formulae and the analysis provide new ways to understand structure-property relationship for β and can hence be used to fine-tune the magnitude of β in a molecule.

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“…At present, the research focus of nonlinear optical materials is mainly focused on the construction of organic molecules containing electron donor (D), electron acceptor (A) and π-conjugation [7]. For example, D-π-A, A-π-D-π-A, D-π-A-π-D and other organic molecules [8] [9], focus on increasing the third-order NLO coefficients (second-order hyperpolarizability), so as to improve the optical properties of organic materials [10] [11] [12].…”

Section: Introductionmentioning

confidence: 99%

Electronic Absorption Spectra and Third-Order Nonlinear Optical Property of Dinaphtho[2,3-b:2’,3’-d]Thiophene-5,7,12,13- Tetraone (DNTTRA) and Its Phenyldiazenyl Derivatives: DFT Calculations

Chen¹,

Zhang²,

He³

et al. 2020

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Third-order nonlinear optical (NLO) materials have broad application prospects in high-density data storage, optical computer, modern laser technology, and other high-tech industries. The structures and frequencies of Dinaphtho[2,3-b:2',3'-d]thiophene-5,7,12,13-tetraone (DNTTRA) and its 36 derivatives containing azobenzene were calculated by using density functional theory B3LYP and M06-2X methods at 6-311++g(d, p) level, respectively. Besides, the atomic charges of natural bond orbitals (NBO) were analyzed. The frontier orbitals and electron absorption spectra of A-G5 molecule were calculated by TD-DFT (TD-B3LYP/6-311++g(d, p) and TD-M06-2X/6-311++g(d, p)). The NLO properties were calculated by effective finite field FF method and self-compiled program. The results show that 36 molecules of these six series are D-π-A-π-D structures. The third-order NLO coefficients γ (second-order hyperpolarizability) of the D series molecules are the largest among the six series, reaching 10 7 atomic units (10 −33 esu) of order of magnitude, showing good third-order NLO properties. Last, the third-order NLO properties of the azobenzene ring can be improved by introducing strong electron donor groups (e.g.-N(CH 3) 2 or-NHCH 3) in the azobenzene ring, so that the third-order NLO materials with good performance can be obtained.

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Solvent effects on static polarizability, static first hyperpolarizability and one- and two-photon absorption properties of functionalized triply twisted Möbius annulenes: a DFT study

Cited by 15 publications

References 66 publications

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

A generalized few-state model for the first hyperpolarizability

Electronic Absorption Spectra and Third-Order Nonlinear Optical Property of Dinaphtho[2,3-b:2’,3’-d]Thiophene-5,7,12,13- Tetraone (DNTTRA) and Its Phenyldiazenyl Derivatives: DFT Calculations

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