Strongly Emissive and Photostable Four-Coordinate Organoboron N,C Chelates and Their Use in Fluorescence Microscopy

Chemistry : a European Journal
Vânia F PaisUwe Pischel

Abstract

Six strongly fluorescent four-coordinate organoboron N,C chelates containing an aryl isoquinoline skeleton were prepared. Remarkably, the fluorescence quantum yields reach values of up to 0.74 in oxygen-free toluene. The strong B-N interaction was corroborated by the single-crystal X-ray analysis of two dyes. The intramolecular charge-transfer character of the fluorophores was evidenced by solvatochromism studies and time-dependent DFT calculations at the PCM(toluene)/CAM-B3LYP/6-311++G(2d,p)//PCM(toluene)/B3LYP/6-311G(2d,p) level of theory. The compounds combine high chemical stability with high photostability, especially when equipped with electron-donating substituents. The strong fluorescence and the large Stokes shifts predestine these compounds for use in confocal fluorescence microscopy. This was demonstrated for the imaging of the N13 mouse microglial cell line. Moreover, significant two-photon absorption cross sections (up to 61 GM) allow the use of excitation wavelengths in the near-infrared region (>800 nm).

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Citations

Oct 5, 2016·The Journal of Organic Chemistry·Denis FrathGilles Ulrich
Dec 23, 2015·Chemistry : a European Journal·Fábio M F SantosPedro M P Gois
Oct 7, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·D SureshPedro T Gomes
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Jun 3, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Mukundam VangaKrishnan Venkatasubbaiah
Jun 11, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ashanul HaqueMuhammad S Khan
May 26, 2020·Chemistry : a European Journal·Fábio M F SantosPedro M P Gois
Jun 15, 2017·Chemistry : a European Journal·Reinhard HechtAgnieszka Nowak-Król
Dec 7, 2019·Beilstein Journal of Organic Chemistry·Vânia F PaisUwe Pischel
Jan 8, 2021·Chemical Communications : Chem Comm·Takumi NakazatoYoshihiro Miyake
Jun 1, 2018·Journal of Chemical Theory and Computation·Maarten T P BeerepootRobert Zaleśny
Sep 17, 2019·The Journal of Organic Chemistry·Zoe DomínguezUwe Pischel
Sep 11, 2020·The Journal of Organic Chemistry·Mariusz TasiorDaniel T Gryko

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