UV spectroscopic studies and charge transfer properties of azobenzene-containing cyclopentadienyliron complexes of arenes: A combined experimental and density functional theoretical study

Li, Guang Lei; Liu, Ji Qiang; Zhao, Bao Dong; Wang, Tao

doi:10.1016/j.saa.2012.11.062

Cited by 12 publications

(4 citation statements)

References 26 publications

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“…Figure 2a shows that the maximum absorption (k max2 ) in the visible light of Fc-diazo-H had a blue shift of 28.1 nm relative to the corresponding Azo-H, and that of Fc-diazo-OMe blue shifted to about 8.7 nm relative to the corresponding Azo-OMe. This phenomenon has been observed in our previous study [49]. The blue shift in k max2 of Fc-diazos means that cationic cyclopentadienyliron moiety is a strong electron-accepting group.…”

Section: One-photon Absorptionsupporting

confidence: 83%

Synthesis and optical properties of a D–A–D cationic cyclopentadienyl iron complex containing double arylazo chromophores

Liu

Jia

Li³

et al. 2014

Res Chem Intermed

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A D-A-D cationic cyclopentadienyl iron complex containing double arylazo chromophores (Fc-diazo) with methoxyl group (Fc-diazo-OMe) was obtained via nucleophilic substitution and well characterized by IR, UV-visible, 1 H NMR, and 13 C NMR spectroscopy, and MS. UV-Vis absorption and nonlinear optical property of Fc-diazo-OMe were investigated by comparison of Fc-diazo with no methoxyl group (Fc-diazo-H). Quantum chemical calculations of the orbital energy, geometric structure of Fc-diazo-OMe, and Fc-diazo-H were conducted by using density functional methods at the B3PW91/Lanl2dz level. Charge transfer from the highest occupied molecular orbital to the lowest unoccupied molecular orbital was found based on density functional theory. The substitution of the methoxyl group greatly improves the NLO property of Fc-diazo. Fc-diazo-OMe shows effective two-photon absorption, coefficient and third-order nonlinear susceptibility for potential applications as optical materials, while Fc-diazo-H barely shows NLO ability.

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Section: One-photon Absorptionsupporting

confidence: 83%

Synthesis and optical properties of a D–A–D cationic cyclopentadienyl iron complex containing double arylazo chromophores

Liu

Jia

Li³

et al. 2014

Res Chem Intermed

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“…The absorption wavelength of PyBN increased in an order of CH 3 CN (454 nm) < CH 2 Cl 2 (462 nm) < DMF (468 nm) < DMSO(472 nm). The positive solvatochromic (bathochromic shift) character upon the increase in solvent polarity demonstrates strong intramolecular charge transfer ability . Thus, rapid photolysis is beneficial for PyBN to exhibit good initiation in acrylate-based radical photopolymerization systems.…”

Section: Results and Discussionmentioning

confidence: 99%

Radical Photopolymerization Using 1,4-Dihydropyrrolo[3,2-b]pyrrole Derivatives Prepared via One-Pot Synthesis

Chen

Liu

et al. 2021

ACS Omega

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Radical photopolymerization has attracted significant attention for manufacturing products with complicated structures. Herein, the synthesized 1,4-bis(4-bromophenyl)-2,5-bis(4-nitrophenyl)-1,4-dihydropyrrole[3,2-b]pyrrole (PyBN) is found to show varying photoactivity upon irradiation at different wavelengths. PyBN affords two main absorption bands, and its maximum absorption peak is at 462 nm, attributing to its strong intramolecular charge transfer property based on the donor–acceptor structure. It efficiently photoinitiates the radical photopolymerization of different (meth)acrylate materials under 365 and 395 nm LED irradiation. The highest double bond conversion of 99.86% is achieved for these materials. Under 470 nm LED, PyBN does not show molecular structure change from photolysis results as a result of intramolecular charge transfer. Therefore, PyBN shows wavelength-selective photoactivity with potential application in dual-wavelength volumetric additive manufacturing. A unique solid product is successfully fabricated using a 365 nm LED with co-irradiation of a 470 nm LED. Additionally, PyBN incorporating camphorquinone (CQ) as a two-component visible light photoinitiator system is investigated under 470 nm LED irradiation. As PyBN has a charge transfer activity at 470 nm, the combination with CQ exhibits a good synergistic interaction. Besides nitro-based PyBN, a methyl-based PyBC was prepared as a reference compound.

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“…Density functional theory (DFT) calculation [20] was carried out to understand the mechanism of the azobenzene photoregulation. Theg round-state geometries of several species participating in the photoregulating process,including cis-/trans-Azo, cis-/trans-Azo + ,and diisobutyronitrile radical/ anion (RC/R À ), were optimized using the DFT/B3LYP/PCM method (Supporting Information, Figure S13).…”

Section: Angewandte Chemiementioning

confidence: 99%

Switchable Reversible Addition–Fragmentation Chain Transfer (RAFT) Polymerization with the Assistance of Azobenzenes

Nie

Qian

et al. 2019

Angewandte Chemie

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Modulating controlled radical polymerization is an interesting and important issue.H erein, modulating RAFT polymerization employing photosensitive azobenzenes is achieved. In the presence of azobenzenes and with visible light off, RAFT polymerization runs smoothly and follows ap seudofirst-order kinetics.I nc ontrast, with light on, RAFT polymerization is greatly decelerated or quenched depending on the type and concentration of azobenzenes.S witchable RAFT polymerization of different (meth)acrylate monomers alternatively with light off and on is demonstrated. Am echanism of photoregulating RAFT polymerization involving radical quenching by azobenzenes is proposed.

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UV spectroscopic studies and charge transfer properties of azobenzene-containing cyclopentadienyliron complexes of arenes: A combined experimental and density functional theoretical study

Cited by 12 publications

References 26 publications

Synthesis and optical properties of a D–A–D cationic cyclopentadienyl iron complex containing double arylazo chromophores

Synthesis and optical properties of a D–A–D cationic cyclopentadienyl iron complex containing double arylazo chromophores

Radical Photopolymerization Using 1,4-Dihydropyrrolo[3,2-b]pyrrole Derivatives Prepared via One-Pot Synthesis

Switchable Reversible Addition–Fragmentation Chain Transfer (RAFT) Polymerization with the Assistance of Azobenzenes

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