Synthesis and Host-Guest Chemistry of Chiral Spirobifluorene-Based Macrocycles Soluble in Basic Aqueous Solution

Kotoko Nakagawa; Kanaru Akimoto; Bunta Nakayasu; Saki Nagashima; Mamoru Tobisu; Michael P Schramm; Shinobu Aoyagi; Toru Amaya

doi:10.1021/acs.orglett.3c02074

Synthesis and Host-Guest Chemistry of Chiral Spirobifluorene-Based Macrocycles Soluble in Basic Aqueous Solution

Org Lett. 2023 Aug 18;25(32):5969-5973. doi: 10.1021/acs.orglett.3c02074. Epub 2023 Aug 4.

Authors

Kotoko Nakagawa¹, Kanaru Akimoto², Bunta Nakayasu², Saki Nagashima¹, Mamoru Tobisu^{2

3}, Michael P Schramm^{1

4}, Shinobu Aoyagi¹, Toru Amaya^{1

2}

Affiliations

¹ Department of Information and Basic Science, Graduate School of Science, Nagoya City University, 1 Yamanohata, Mizuho-cho, Mizuho-ku, Nagoya, Aichi 467-8501, Japan.
² Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
³ Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan.
⁴ Department of Chemistry and Biochemistry, California State University Long Beach (CSULB), 1250 Bellflower Blvd., Long Beach, Los Angeles, California 90840, United States.

PMID: 37540115
DOI: 10.1021/acs.orglett.3c02074

Abstract

Synthesis and host-guest chemistry of water-soluble (pH 12.5) chiral spirobifluorene-based macrocycles 2-[n] were carried out. Cationic guests, such as quaternary ammonium salts, were accommodated well in the hosts. Cp₂Co⁺ was especially strongly bound in 2-[4] (K_a of up to 3.0 × 10⁵ M^-1). Enantioselective recognition with (l)-carnitine was also achieved.