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Data-driven Electrochemical One-pot Synthesis of Double Hetero[7]dehydrohelicene (Supporting Information)

Version 2 2023-10-23, 06:49
Version 1 2023-10-23, 06:30
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posted on 2023-10-23, 06:49 authored by Mohamed S. H. Salem, Rubal SHARMA, Md. Imrul KHALID, Meghna SASI, Ryo AMASAKI, Yoshitane IMAI, Mitsuhiro ARISAWA, Shinobu TAKIZAWA

The pursuit of chiral nanographenes with robust chiral stability and good chiroptical responses is of great interest for material-based applications. However, the most reported preparation processes involve intricate synthetic pathways and harsh conditions, resulting in readily epimerization due to their low epimerization barriers. In this study, we present a streamlined one-pot electrochemical synthesis for a novel double oxaza[7]dehydrohelicene, characterized by a substantial epimerization barrier (33.8 kcal mol−1) and notable chiroptical responses (|glum| = 1.5 × 10−3). To optimize the electrochemical conditions efficiently, we applied a Bayesian optimization (BO) approach with expected improvement (EI) or lower confidence bound (LCB) as an acquisition function, aiming to maximize exploration and exploitation while minimizing the number of experiments needed to identify global maxima. Additionally, the structural and optical features of this molecule have been studied using X-ray crystallographic analysis, and the absorption and emission behaviors were rationalized based on DFT calculations.

Funding

Digitalization-driven Transformative Organic Synthesis (Digi-TOS)

Japan Society for the Promotion of Science

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Implementation of machine-learning-assisted simultaneous multiparameter screening for flow/electrochemical domino reactions

Japan Society for the Promotion of Science

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Development of asymmetric C-C bond formation reaction based on the creation of highly active base metal composite catalyst with low environmental load

Japan Society for the Promotion of Science

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Creation of an innovative molecular conversion method induced by electricity, light, and magnetic field

Japan Science and Technology Agency

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Hoansha Foundation

History

Corresponding author email address

taki@sanken.osaka-u.ac.jp

Copyright

© 2023 The Author(s).

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