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Volumn 130, Issue 52, 2008, Pages 17812-17825

Axially chiral β, β-bisporphyrins: Synthesis and configurational stability tuned by the central metals

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CATALYSIS; BIOMIMETIC STUDY; BISPORPHYRINS; BORONIC ACID; BORYLATION; CENTRAL METALS; CHIRAL PHASE; CHIRAL RECOGNITION; CONFIGURATIONAL STABILITY; ELECTRON TRANSFER PROCESS; HPLC-CD; METALATION; OXIDATION POTENTIALS; PERIPHERAL POSITIONS; QUANTUM CHEMICAL; QUANTUM CHEMICAL CALCULATIONS; ROTATIONAL BARRIERS; SUBSTITUTION PATTERNS; SUZUKI-MIYAURA COUPLING; TETRAPYRROLE;

EID: 58849101382     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8055886     Document Type: Article
Times cited : (91)

References (157)
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    • In our hands these conditions published for the synthesis of meso-boronic acid esters of TAPs by Hyslop et al. did give β-borylated TAPs starting from the respective β-brominated porphyrins, too, but in very low yields e.g, 25-30% for 3a as compared to 70% with our optimized procedure, Table 1, entries 1 and 8
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    • The new dimers described in this paper are configurationally not as stable as the meso,meso'-linked bisporphyrins previously reported.31 The synthesis ofβ,β'-bisporphyrins with additionalβ-substituents next to the central axis is currently in progress in our group
    • 31 The synthesis ofβ,β'-bisporphyrins with additionalβ-substituents next to the central axis is currently in progress in our group.
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    • Regarding the rotational barriers the calculations fail to differentiate between the Pd/Pd and the Cu/Cu dimer, certainly because the Pd/Pd complex should be influenced by relativistic effects that can not be taken into account with the used methods
    • Regarding the rotational barriers the calculations fail to differentiate between the Pd/Pd and the Cu/Cu dimer, certainly because the Pd/Pd complex should be influenced by relativistic effects that can not be taken into account with the used methods.
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    • It is tempting to interpret this potential splitting as being due to different electronic 'communication' between the two porphyrin subunits, also because many other factors like, e.g, ion pairing effects, control the redox splitting significantly.68 On the other hand, Arnold et al. 69 observed an analogous behavior for butadiyne-bridged metalated octaethyl-substituted bis(octaethylporphyrins) and attributed this wave splitting to aggregate formation of cationic porphyrin units.70 Despite the apparent steric hindrance by the meso substituents it might indeed be imaginable that the meso-aryl substituted bisporphyrins in this paper may form aggregates
    • 70 Despite the apparent steric hindrance by the meso substituents it might indeed be imaginable that the meso-aryl substituted bisporphyrins in this paper may form aggregates.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.