Smart Network Polymers with Bis(piperidyl)naphthalene Cross-Linkers: Selective Fluorescence Quenching and Photodegradation in the Presence of Trichloromethyl-Containing Chloroalkanes

• Published in: Macromolecules Vol. 50; no. 9; pp. 3544 - 3556
• Main Authors: Sasaki, Shunsuke, Sugita, Yoshiyuki, Tokita, Masatoshi, Suenobu, Tomoyoshi, Ishitani, Osamu, Konishi, Gen-ichi
• Format: Journal Article
• Language: English
• Published: American Chemical Society 09.05.2017
• Subjects: chloroform; crosslinking; fluorescence; gels; naphthalene; photolysis; polymers; solvents; storage modulus
• ISSN: 0024-9297; 1520-5835; 1520-5835
• DOI: 10.1021/acs.macromol.7b00213

1,4-Bis­(piperidyl)­naphthalene (1,4-BPN) was employed as a cross-linker for poly­(n-butyl methacrylate) gels to generate soft materials that exhibit selective fluorescence quenching and photodegradation in 1,1,1-trichloromethyl-containing chloroalkanes. In chloroform and 1,1,1-trichloroethane, 1,4-BPN is subject to efficient fluorescence quenching via the formation of exciplexes, which results in rapid photodegradation. Similarly, poly­(n-butyl methacrylate) gels cross-linked with 1,4-BPN were highly fluorescent and stable in various organic solvents and chloroalkanes but exhibited less intense fluorescence and rapid photodegradation in 1,1,1-trichloromethyl-containing chloroalkanes. Upon swelling in 1,1,1-trichloroethane, these gels exhibited a steep drop in the storage modulus during first 10 s of photoirradiation (λ = 365 nm). Further photoirradiation for 10–30 min led to the decomposition of the gels. Thus, we propose that the 1,4-BPN-based cross-linker can be used for the facile preparation of diverse polymeric materials with synergistic fluorescence, detection, and photodecomposition properties toward unreactive and neutral analytes.