We reported a visible-near-infrared fluorescent probe for peroxynitrite detection with large pseudo-Stokes and emission shifts, based on through-bond energy transfer (TBET) in combination with intramolecular charge transfer (ICT).
Ag eneral strategy is reported for developing through-bond energy transfer (TBET) fluorescence probes by combining intramolecular charge transfer (ICT). The strategy uses ac oplanard onor-p-bridge-acceptor system (SiOPh-PyOH) without spirolactam. The off-on switcho fT BET and ICT is controlledb yc oplanar structurec hanges in the sensing process insteado fs pirolactam ring-opening in traditional TBET probes. DFT calculations showed that the energy and charget ransfers from SiOPh to PyOH are prohibited.Since the SiOPh has no fluorescence, the probe SiOPh-PyOH shows fluorescence propertiess imilart ot hat of pyrene.After sensing ONOO À ,t he silyl ether is removed and the probec hanges into À OPh-PyO À .E lectron-donating ICT from À OPh to PyO À inducesalarge redshift of emission to 594 nm (179 nm shift). TBET from À OPht oP yO À ensures the probe exhibits al arge pseudo-Stokes shift of 213 nm. Furthermore, the probe was successfully used in endogenousO NOO À detection. This study offersanew strategy for the construction of TBET probes emitting in the red region without spirolactam ring-opening, an ew ONOO À sensing system using silyl ether as ar eaction site, and am ethod for the deprotection of silyl ethers with ONOOH under mild conditions.[a] Dr.
The peroxynitrite ion (ONOO−) has important roles in many biological processes. We have developed a multicolor ONOO−‐sensing probe (SiONNOH) that undergoes deprotonation and desilylation processes, which result in several changes in the emission wavelengths. In response to different concentrations of ONOO−, the probe exhibits fluorescence changes from pink (595 nm at 2 eq. ONOO−) to green (540 nm at 6 eq. ONOO−) via orange (3 eq. ONOO−) and yellow (4 eq. ONOO−) under physiological conditions until no fluorescence signal is observed after ONOO− is completely eliminated by lipoic acid. The probe shows the high selectivity for ONOO− and the limit of detection is calculated to be 1.27 μM. Moreover, the probe shows the capacity to monitor the concentration ranges of ONOO− through multicolor fluorescence in living cells, which will greatly facilitate the rapid detection of ONOO− concentration ranges by the naked eye under a UV light without any precision instrumentation.
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