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Oligoboroxine-based architectures

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Abstract

Boroxines are well-known six-membered ring compounds and their fundamental properties such as aromaticity, Lewis acidity, photophysical property, interactions with anions, thermal stability, and reactivity have been investigated. Since the 2000s, boroxine formation has been paid much attention as a reversible covalent bond formation. Boronic acids (RB–(OH)2) reversibly trimerize to afford the tripodal structure of boroxines. The equilibrium between boronic acids and boroxines can be controlled simply by the addition or removal of water. The addition of N-donor Lewis bases also promotes the reversible formation of boroxine⋅N-donor Lewis base adducts. To date, by using this unique reversible trimerization, various self-assembled boroxine-based covalent architectures and polymeric materials have been reported. Boroxine-based architectures are categorized into three types as follows. (a) Tripodal structures by monoboroxine formation, (b) network structures by polyboroxine formation including covalent organic frameworks (= COFs) and dynamic polymer materials, and (c) discrete structures by oligoboroxine formation. Compared to mono or polyboroxine-based architectures (a) or (b), oligoboroxine-based discrete architectures (c) containing a precise number of boroxines are an emerging research subject and have the potential to create a novel type of discrete covalent architectures. Thus, in this review, we summarize recent progress including our works in this field.

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Acknowledgements

K.O. greatly appreciates the committee members of Association of Research for Host–Guest and Supramolecular Chemistry (Japan) for awarding “SHGSC Japan Award of Excellence 2020”. The studies in this review were supported by a CREST (Core Research for Evolution Science and Technology) project from the Japan Science and Technology Agency (JST) and JSPS KAKENHI Grant Number 15H05800 and 25410087. The authors are also deeply grateful to all the group members who developed the studies in this review. This is a paper selected for the “SHGSC Japan Award of Excellence 2020”

Funding

Core Research for Evolution Science and Technology (CREST) project from the Japan Science and Technology Agency (JST). JSPS KAKENHI Grant Number 15H05800 and 25410087.

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  1. Department of Chemistry, Tokyo Institute of Technology, O-okayama Meguro-ku, 2-12-1, Tokyo, 152-8551, Japan

    Kosuke Ono & Nobuharu Iwasawa

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Ono, K., Iwasawa, N. Oligoboroxine-based architectures. J Incl Phenom Macrocycl Chem 101, 19–29 (2021). https://doi.org/10.1007/s10847-021-01074-6

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