4.6 Article

Switching of Two-Photon Optical Properties by Anion Binding of Pyrrole-Based Boron Diketonates through Conformation Change

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 15, Pages 3404-3410

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201905467

Keywords

anion binding; conformation changes; non-linear optics; sensors; two-photon absorption

Funding

  1. JSPS KAKENHI [JP18H01943, JP26288042, JP18H01968]
  2. MEXT [JP26107004, JP26107007]
  3. Ritsumeikan Global Innovation Research Organization (R-GIRO) project [2017-22]

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Two-photon absorption (TPA) dyes with intense fluorescence can be used to detect small chemical species and as sensors and bioimaging probes for specific analytes. Various TPA dyes responding to a number of external stimuli have been reported. Among them, biologically important anionic species have not been used as agents to control TPA properties because their direct electronic influences on the transition dipole moments of dyes are typically small. In this study, dipyrrolyldiketone BF2 complexes substituted with pi-extended units exhibited efficient TPA properties that could be regulated by conformation changes induced by anion binding. The TPA intensity decreased to 1/5 of the original intensity upon anion binding, which was much larger than that observed for one-photon absorption. Anion detection was achieved by a change in the emission intensity of spatially resolved spots of two-photon-excited fluorescence (TPEF) in the sample. Experimental and theoretical studies were performed to understand the mechanism of the TPA property control and showed that the drastic changes in the transition dipole moments upon conformation changes between the straight and bending forms of the pi-electronic systems caused the TPA and TPEF intensities drop.

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