Design, Synthesis, and Function of Novel Stimuli-Responsive Two- Photon Absorbing Molecules

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We designed and synthesized stimuli-responsive π-conjugated molecules that include (i) pyridine nucleus as a stimuli-responsive part, (ii) ethynyl moiety as a rigid π-bridge, and (iii) terminal aniline derivatives as an electron donor part. The synthesized molecules have high fluorescence quantum yields and high thermal stability as well as high two-photon absorbing abilities. N-quaternization of the pyridine unit caused large optical changes such as bathochromicshift of the absorption spectra, quenching of the fluorescence emission, and somewhat enhanced two-photon absorption. Their use in biological imaging or for photodynamictherapy (PDT) is highly expected. A N-methylpyridium triflate derivative was found to function as anexcellent fluoride ion-selective anion sensor, while N-free parent pyridine derivatives can be a Fe3+ion-selective sensor