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Porphyrindiene-Based Tandem Diels-Alder Reaction for Preparing Low-Symmetry pi-Extended Porphyrins with Push-Pull Skeletons
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- Cao, Guanyue (author)
- East China Univ Sci & Technol, Peoples R China
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- Baryshnikov, Glib (author)
- Linköpings universitet,Laboratoriet för organisk elektronik,Tekniska fakulteten
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- Chen, Chen (author)
- East China Univ Sci & Technol, Peoples R China
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- Chen, Liyuan (author)
- East China Univ Sci & Technol, Peoples R China
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- Zhao, Tengjiao (author)
- East China Univ Sci & Technol, Peoples R China
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- Fu, Shuyi (author)
- East China Univ Sci & Technol, Peoples R China
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- Jiang, Zhenhui (author)
- East China Univ Sci & Technol, Peoples R China
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- Liu, Xiujun (author)
- East China Univ Sci & Technol, Peoples R China
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- Li, Qizhao (author)
- East China Univ Sci & Technol, Peoples R China
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- Xie, Yongshu (author)
- East China Univ Sci & Technol, Peoples R China
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- Li, Chengjie (author)
- East China Univ Sci & Technol, Peoples R China
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(creator_code:org_t)
- 2022-06-24
- 2022
- English.
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In: Journal of Organic Chemistry. - : AMER CHEMICAL SOC. - 0022-3263 .- 1520-6904. ; 87:14, s. 9001-9010
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- Tandem Diels-Alder reactions of masked porphyrindienes (i.e., sulfolenoporphyrins) with benzoquinones and stilbenes, followed by aromatization, have been developed to load porphyrin with mixed annulation units (i.e., terphenyl and naphthoquinone), furnishing the low-symmetry pi-extended porphyrins (DxAy) with push-pull skeletons. All low-symmetrical chromophores display panchromatic absorption spectra, which look like a spectral combination of symmetrical congeners (D4/A4) in a certain ratio. Among them, tD2A2 with trans-arrangement of push/pull units possesses the largest maximum centered at 766 nm with the onset around 900 nm. The fusion of the electron-deficient naphthoquinone moiety on the porphyrin core results in the approximately quantitative regulation of the E-ox1 and HOMOs (i.e., 0.10-0.13 V increase for the E-ox1 and 0.14-0.16 eV decrease for the HOMOs per naphthoquinone unit). In brief, this work provides a new way to construct low-symmetry pi-extended porphyrins with tunable properties resorting to the ratios and locations of the annulated push-pull units.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Cao, Guanyue
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Baryshnikov, Gli ...
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Chen, Chen
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Chen, Liyuan
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Zhao, Tengjiao
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Fu, Shuyi
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show more...
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Jiang, Zhenhui
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Liu, Xiujun
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Li, Qizhao
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Xie, Yongshu
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Li, Chengjie
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show less...
- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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and Organic Chemistr ...
- Articles in the publication
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Journal of Organ ...
- By the university
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Linköping University