1985
DOI: 10.1002/anie.198503391
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Sealing and Opening Porous Monolayer Vesicle Membranes

Abstract: In THF at room temperature, 1 reacts with less reactive dienophiles such as 7 -11 (Table 1) to give the cycloadducts 12[61 in high yield; intermediate radical ions are not detected. The adducts 12a -12d split off two equivalents of dimethylamine at 140-160°C under acid catalysis with formation of the compounds 13a-13d (yield 50-70%).

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Cited by 33 publications
(6 citation statements)
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“…Enhancement of the stability and robustness of these self-organized structures may rely on a combination of different intermolecular interactions. [10,11] Inspired by the early work of Fuhrhop et al and Ringsdorf and co-workers on the self-organization of bola-amphiphiles, [12,13] we have introduced rigid mesogenic groups or strong p-p-stacking moieties into bolaamphiphiles, resulting in significantly enhanced stability of the self-assembled structures. [14,15] In this Communication, we describe the design and synthesis of a new bola-amphiphile with two carboxylic acid end groups and a diketopyrrolopyrrole (DPP) chromophore in the central part.…”
mentioning
confidence: 99%
“…Enhancement of the stability and robustness of these self-organized structures may rely on a combination of different intermolecular interactions. [10,11] Inspired by the early work of Fuhrhop et al and Ringsdorf and co-workers on the self-organization of bola-amphiphiles, [12,13] we have introduced rigid mesogenic groups or strong p-p-stacking moieties into bolaamphiphiles, resulting in significantly enhanced stability of the self-assembled structures. [14,15] In this Communication, we describe the design and synthesis of a new bola-amphiphile with two carboxylic acid end groups and a diketopyrrolopyrrole (DPP) chromophore in the central part.…”
mentioning
confidence: 99%
“…1989Lett. , 30, 2391 Me2CuLi \^ou CH3 CH3 CH3CH3 (7) (a) House, H. O.; Respess, W. L.; Whitesides, G. M. J. Org. Chem.…”
mentioning
confidence: 99%
“…* Address correspondence concerning design and synthesis to G. W.G. and concerning NMR and kinetics to L.E 7. On leave from Toa University, Shimonoseki, Japan.…”
mentioning
confidence: 99%
“…Bolaform amphiphiles are molecules containing two hydrophilic moieties connected by a hydrophobic chain. 2 They can also be viewed as two conventional amphiphiles covalently linked via their hydrophobic chain ends. In diluted solutions, they may form elongated, threadlike and platelike micelles.…”
Section: Introductionmentioning
confidence: 99%