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Tuning the Optical ...
Tuning the Optical Properties of 1,1'-Biphospholes by Chemical Alterations of the P-P Bridge
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- Arkhypchuk, Anna I. (författare)
- Uppsala universitet,Molekylär biomimetik
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- Orthaber, Andreas (författare)
- Uppsala universitet,Molekylär biomimetik
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- Ott, Sascha (författare)
- Uppsala universitet,Molekylär biomimetik
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(creator_code:org_t)
- 2014-01-02
- 2014
- Engelska.
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Ingår i: European Journal of Inorganic Chemistry. - : Wiley. - 1434-1948 .- 1099-1948 .- 1099-0682. ; 2014:10, s. 1760-1766
- 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
- 2,5-Di(1-naphthyl)-1-phenylphosphole (2) was prepared from phenylphosphine and dinaphthylbutadiyne in 70% yield, and oxidized to its oxide 3. Treatment of 2 with a solution of potassium naphthalide results in selective formation of phospholide anion 4, which can be oxidized with iodine to afford biphosphole 5. The crystal structure of 5 exhibits an unusual s-trans conformation across the P-P bridge that is most stabilized by - stacking of the naphthyl substituents. Biphosphole 5 can be oxidized to its mono-oxidized 6 and dioxide 7. Generally, all phosphole oxidations lead to decreased pyramidalization of the P centres and, consequently, to significantly redshifted lowest-energy absorption maxima. Mono-oxidized biphosphole 6, which consists of an ordinary phosphole and an electron-deficient oxidized phosphole, features a unique low-energy optical transition (shoulder at 430 nm), which is tentatively assigned to a charge-transfer transition. The UV/Vis spectrum of dioxide 7 lacks this transition. At the same time, the emission maximum of 7 is bathochromically shifted by 80 nm relative to that of 5.
Nyckelord
- Phosphorus heterocycles
- Charge transfer
- Conjugation
- Pi interactions
- Aromaticity
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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