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Title
Japanese: 
English:Two‐step Conformational Control of a Dibenzo Diazacyclooctane Derivative by Stepwise Protonation 
Author
Japanese: 石割 文崇, S. Miyake, 井上 恵希, K. Hirose, 福島 孝典, A. Saeki.  
English: F. Ishiwari, S. Miyake, K. Inoue, K. Hirose, T. Fukushima, A. Saeki.  
Language English 
Journal/Book name
Japanese: 
English:Asian Journal of Organic Chemistry 
Volume, Number, Page Vol. 10        Page 1-6
Published date Apr. 1, 2021 
Publisher
Japanese: 
English: 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
Official URL https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202100154
 
DOI https://doi.org/10.1002/ajoc.202100154
Abstract The conformational control of a dibenzo‐1,5‐diazacyclooctane (DACO) derivative with tertiary and secondary amino groups by stepwise protonation is investigated by single crystal X‐ray diffraction analysis, computational simulation, and variable temperature NMR measurements. The DACO derivative undergoes two‐step protonation, to afford bent‐shape monoprotonated and diprotonated species, whose conformations are different from each other. The monoprotonated form is characterized by a Tröger's‐base‐like proton‐bridged pseudo bicyclic structure, while the diprotonated form features a deformed boat‐shape eight membered ring structure. The degree of bending and conformational rigidity of the DACO skeleton become higher as the degree of the protonation is increased. Such a multistep conformational control of the DACO derivative would be useful for developing new stimuli responsive supramolecular systems that exhibit a multistep change in properties.

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