TY - JOUR A1 - Alnajjar, M. A. A1 - Bartelmeß, Jürgen A1 - Hein, R. A1 - Ashokkumar, Pichandi A1 - Nilam, M. A1 - Nau, W. M. A1 - Rurack, Knut A1 - Hennig, A. T1 - Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril N2 - We introduce herein boron-dipyrromethene (BODIPY) dyes as a new class of fluorophores for the design of reporter dyes for supramolecular host–guest complex formation with cucurbit[7]uril (CB7). The BODIPYs contain a protonatable aniline nitrogen in the meso-position of the BODIPY chromophore, which was functionalized with known binding motifs for CB7. The unprotonated dyes show low fluorescence due to photoinduced electron transfer (PET), whereas the protonated dyes are highly fluorescent. Encapsulation of the binding motif inside CB7 positions the aniline nitrogen at the carbonyl rim of CB7, which affects the pKa value, and leads to a host-induced protonation and thus to a fluorescence increase. The possibility to tune binding affinities and pKa values is demonstrated and it is shown that, in combination with the beneficial photophysical properties of BODIPYs, several new applications of host–dye reporter pairs can be implemented. This includes indicator displacement assays with favourable absorption and emission wavelengths in the visible spectral region, fluorescence correlation spectroscopy, and noncovalent surface functionalization with fluorophores. KW - BODIPY KW - Cucurbituril KW - Fluorescence KW - PH KW - Photoinduced Electron Transfer KW - Supramolecular Chemistry PY - 2018 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:kobv:b43-456361 UR - https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-14-171.pdf SN - 1860-5397 VL - 14 SP - 1961 EP - 1971 PB - Beilstein-Institut CY - Frankfurt a. M. AN - OPUS4-45636 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER -