Research on Combinatorial Functions of Integrated Organic Redox Systems and their Applications for Unimolecular Memory

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This project has been planned to develop new design concepts on the novel organic responding molecules based on the integration of redox active molecules. The major themes to be tackled with are as follows : (1) Redox response systems with electrochemical bistability and surface modifying properties ; (2) New synthetic strategy for the fused- polyether structures ; (3) Redox active molecules with phase transition properties triggered by external stimuli.We have succeeded in preparing redox systems to meet the requirement in the first theme, and some of them are further endowed with multi-input and multi-output fuctionalities. The disuflide unit or ethynyl groups were selected that act as surface-binding linkers for Au an Si, respectively. Preparation of SAM and examination toward the realization of unimolecular memory are now under way.The fused-polyether skeleton found in some marine natural products should be a suitable motif for studying the aggregation by weak C-H--O hydrogen bonds … More . In the second theme, facile and general convergent strategy was developed for a variety of polyether skeleton. Based on the newly developed protocol based on the reaction between an aldehyde and an acylanion equivalent, we could synthesize polyetheral natural product (hemibrevetoxin B) and the large segments of ciguatoxins with 4-5 ether units. X-ray analyses on some of them have revealed that several short C-H--O contacts were observed that connect tape-shaped polyethers tol the stacked or dimeric strucures. Not only natural but also non-natural polyethers are shown worth investigated.Reversible oligomerization of bis(diarylethenyl)arenes-type electron donors upon oxidation is the outstanding achievement in terms of the third theme. Deeply-colored polycation oligomers could be isolated as stable salts that regenerated the starting monomeric donors upon reduction. By attaching long alkyl chains on the aryl groups, some of these materials act as organic gelators, thus giving a new desing concept for the dynamic mesophase, whose properties can be modulated by electrochemical input. Less