Bolaphiles unsymmetrical

Figure 4. Unsymmetrical bolaphiles synthesized for the generation of monolayer rods and tubules.

Fuhrhop et al.35 demonstrated that incorporation of quinone moieties into either the head groups or within the hydrophobic spacer of a bolaphile gave redox-active membranes (Figure 9). Unsymmetrical bo-laamphiphiles were used as models for photosynthetic electron acceptors (e.g. 29) and vesicle formation was verified by electron micrograph. The anticipated membrane organization would position the quinone moieties on the vesicle exterior. The location of the quinone moieties in this series was verified by their quantitative reduction by borohydride. Since boro-hydride does not diffuse through lipid membranes these membrane quinones must be part of the vesicle exterior. 

Scheme 2. The unsymmetrical bolaphiles synthesized by Fuhrhop et al. [17] for the generation of mono-layer rods and tubules.

Fuhrhop et al. demonstrated [26] that placing quinone moieties in either the head groups or within the hydrophobic spacer, formed redox-active membranes thus, unsymmetrical bolaphile 6 (Scheme 3) is a model of electron acceptors in photosynthesis and forms vesi-... 

Scheme 3. The unsymmetrical bolaphile 6 was used to fix the quinone functionality at the surface of the micelle whereas, 7 and 8 were used to position the quinone moiety within the membrane.

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See also in sourсe #XX -- [ ]

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