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Rational constructi...
Rational construction of perylenequinone annulated porphyrins via cycloaddition reactions
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- Ma, Wenjing (författare)
- East China Univ Sci & Technol, Peoples R China
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- Chen, Chen (författare)
- East China Univ Sci & Technol, Peoples R China
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- Qin, Zhonghe (författare)
- Univ Calif Irvine, CA 92697 USA
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- Zhu, Shuhui (författare)
- East China Univ Sci & Technol, Peoples R China
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- Qiu, Ning (författare)
- Shanghai Starriver Bilingual Sch, Peoples R China
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- Baryshnikov, Glib (författare)
- Linköpings universitet,Laboratoriet för organisk elektronik,Tekniska fakulteten
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- Li, Qizhao (författare)
- East China Univ Sci & Technol, Peoples R China
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- Chengjie, Li (författare)
- East China Univ Sci & Technol, Peoples R China
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- Liu, Xiujun (författare)
- East China Univ Sci & Technol, Peoples R China
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(creator_code:org_t)
- ELSEVIER SCI LTD, 2024
- 2024
- Engelska.
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Ingår i: Dyes and pigments. - : ELSEVIER SCI LTD. - 0143-7208 .- 1873-3743. ; 227
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- Acenequinone-fused porphyrins show remarkable long wavelength absorption, low-lying LUMO orbital and uniform pi,pi-stacking, enabling the potential applications as opto-electronic materials and catalysts. At present, the synthesis of large quinone fused porphyrins remains challenging. To address this, the cycloaddition reactions of naphthoquinone-fused porphyrin (Ni4NQ), followed by oxidative aromatization, have been employed. Through Diels-Alder reaction with perylenes in the presence of chloranil, a series of perylenequinone-fused porphyrins (1Ni-4Ni) have been synthesized with an overall yield above 70 %. Later, the tri-adduct 3Ni underwent 1,3-dipolar cycloaddition with nitrile oxide and the following DDQ oxidation to outcome the unsymmetrical tetra-adduct 5Ni. Although the peripheral perylenequinones fusion in 1Ni-4Ni has limited impact on the absorption with respect to the naphthoquinone-fused counterpart Ni4NQ, introduction of an isoxazole via 1,3-cycloaddition (5Ni) leads to a bathochromic Q band. This result has been rationalized by theoretical calculations. Additionally, the incorporation of perylenequinone units gives rise to intense intermolecular pi,pi-stacking and CH-pi interactions within the crystal packing. The self-assembly behavior using a good/bad solvent strategy are structural dependence. The tri-perylenequinone-fused porphyrins 3Ni formed spherical architecture, while tetraperylenequinone-fused porphyrin 4Ni afforded cubic or petal-type assemblies.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- Porphyrins; Perylene; Nitrile oxide; Diels-alder reaction; 3-dipolar cycloaddition; Assembly
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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