- An electron-transfer induced conformational transformation from non-cofacial "sofa" to cofacial "boat" in cyclotetraveratrylene (CTTV) and formation of charge transfer complexes
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Electro-active polychromophoric assemblies that undergo clam-like electromechanic actuation represent an important class of organic functional materials. Here, we show that the readily available cyclotetraveratrylene (CTTV) undergoes oxidation-induced folding, consistent with interconversion from a non-cofacial "sofa" conformation to a cofacial "boat" conformer. It is found that the non-cofacial "sofa" conformer of CTTV forms stable electron donor-acceptor complexes with chloranil and DDQ. Electron-transfer induced conformational transformation in CTTV provides a framework for the rational design of novel organic functional molecules.
- Wang, Denan,Ivanov, Maxim V.,Mirzaei, Saber,Lindeman, Sergey V.,Rathore, Rajendra
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supporting information
p. 5712 - 5717
(2018/08/17)
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- Inclusion chemistry of cyclotetracatechylene
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The synthesis and X-ray crystal structures of the first inclusion complexes of cyclotetracatechylene (CTTC, 1) are reported.Crystals grown from a dimethylformamide (DMF) solution of 1 contain a total of six DMF molecules per CTTC unit (1*6DMF, 5) whilst crystals obtained from methanol in the presence of pyridine vapour form as a 1:2:2 complex (1*2pyridine*2methanol, 6).Hydrogen-bonded interactions between host and guest(s) play an important role in the molecular structure and, in the case of 6, a terminated eleven-atom hydrogen bonded chain is observed.
- Barbour, Leonard J.,Steed, Jonathan W.,Atwood, Jerry L.
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p. 857 - 860
(2007/10/02)
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- Cyclo-oligomerization of veratryl alcohol with triflouroacetic acid
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Treatment of veratryl alcohol with a dilute solution of triflouroacetic acid in chloroform yields a mixture of oligomers. Four major products have been separated and identified as the new cyclohexaveratrylene 6 and cyclopentaveratrylene 5, in addition to the known cyclic tetramer 4 and cyclic trimer 3.
- Al-Farhan, Emile,Keehn, Phillip M.,Stevenson, Robert
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p. 3591 - 3594
(2007/10/02)
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- Electrochemical Oxidation of Aromatic Ethers. Part 6. Oxidation of 4-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline and Attempted Synthesis of 4-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,4-dihydro-3(2H)-isoquinoline
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The cyclisation of 3-(2,4-dimethoxybenzyl)-2-(2-hydroxymethyl-4,5-dimethoxyphenyl)-N-methylpropionamide (5) and related compounds does not yield 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-1,4-dihydro-3(2H)-isoquinolone, but gives instead dibenzocycloheptane derivatives.Anodic oxidation of 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline affords the corresponding 3,4-dihydroisoquinolinium and 4-(3,4-dimethoxybenzylidene)-6,7-dimethoxy-2-methyl-1,4-dihydroisoquinolinium salts.No intramolecularly aryl-aryl coupled products are isolated and the implication of this result on the design of substrates for the synthesis of biphenyl derivatives is discussed.
- Carmody, Maurice P.,Sainsbury, Malcolm,Newton, Roger F.
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p. 2013 - 2020
(2007/10/02)
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