| Autor: |
Jin E; Max Planck Institute for Polymer Research, Mainz 55128, Germany., Yang Q; Max Planck Institute for Polymer Research, Mainz 55128, Germany., Ju CW; Max Planck Institute for Polymer Research, Mainz 55128, Germany.; College of Chemistry, Nankai University, Tianjin 300071, China., Chen Q; Max Planck Institute for Polymer Research, Mainz 55128, Germany., Landfester K; Max Planck Institute for Polymer Research, Mainz 55128, Germany., Bonn M; Max Planck Institute for Polymer Research, Mainz 55128, Germany., Müllen K; Max Planck Institute for Polymer Research, Mainz 55128, Germany.; Institute of Physical Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, Mainz 55128, Germany., Liu X; Max Planck Institute for Polymer Research, Mainz 55128, Germany., Narita A; Max Planck Institute for Polymer Research, Mainz 55128, Germany.; Organic and Carbon Nanomaterials Unit, Okinawa Institute of Science and Technology Graduate University, Kunigami-gun, Okinawa 904-0495, Japan. |
| Abstrakt: |
Dibenzo[ hi , st ]ovalene (DBOV) has excellent photophysical properties, including strong fluorescence and high ambient stability. Moreover, the optical blinking properties of DBOV have enabled optical super-resolution single-molecule localization microscopy with an imaging resolution beyond the diffraction limit. Various organic and inorganic fluorescent probes have been developed for super-resolution imaging, but those sensitive to pH and/or metal ions have remained elusive. Here, we report a diaza-derivative of DBOV (N-DBOV), synthesized in eight steps with a total yield of 15%. Nitrogen (N)-bearing zigzag edges were formed through oxidative cyclization of amino groups in the last step. UV-vis and fluorescence spectroscopy of N-DBOV revealed its promising optical properties comparable to those of the parent DBOV, while cyclic voltammetry and density functional theory calculations highlighted its lower orbital energy levels and potential n -type semiconductor character. Notably, in contrast to that of the parent DBOV, the strong luminescence of N-DBOV is dependent on pH and the presence of heavy metal ions, indicating the potential of N-DBOV in sensing applications. N-DBOV also exhibited pH-responsive blinking, which enables pH-sensitive super-resolution imaging. Therefore, N-DBOV appears to be a highly promising candidate for fluorescence sensing in biology and environmental analytics. |
