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Synthesis of Water‐Soluble Triazinophanes and Evaluation of Their Molecular Recognition Properties
Author(s) -
Kusano Shuhei,
Konishi Sae,
Ishikawa Ryuta,
Sato Norihiro,
Kawata Satoshi,
Nagatsugi Fumi,
Hayashida Osamu
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601663
Subject(s) - chemistry , anthracene , molecular recognition , pyrene , cationic polymerization , derivative (finance) , triazine , titration , aqueous solution , fluorescence , supramolecular chemistry , combinatorial chemistry , molecule , polymer chemistry , organic chemistry , physics , quantum mechanics , financial economics , economics
Molecular recognition properties of water‐soluble triazinophane 1a – 1c , derivatized through the straightforward S N Ar reaction of common intermediate 5 , were explored in aqueous media. Fluorescence titration of 1a – 1c by using mono cationic aromatic hydrocarbon G1 and G2 as guests revealed that 1 prefers to form a host–guest complex with pyrene derivative G2 rather than anthracene derivative G1 . Complex formation between the derivatives of 1 and G2 were in a 1:1 equimolar ratio with binding constants of ≈ 8 × 10 3 ( m –1 ), regardless of the substitution groups on the triazine rings. In addition, we found that the molecular recognition of 1 was successfully fine‐tuned through post‐modification of the triazine rings. With dicationic anthracene G3 as a guest only 1b formed a host–guest complex ( K a = 5.5 × 10 3 m –1 ).