2015
DOI: 10.1002/chem.201504133
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Molecular Insight into Long‐Wavelength Fluorogenic Dye Design: Hydrogen Bond Induces Activation of a Dormant Acceptor

Abstract: The detection of chemical or biological analytes in response to molecular changes relies increasingly on fluorescence methods. Therefore, there is a substantial need for the development of improved fluorogenic dyes. In this study, we demonstrated how an intramolecular hydrogen bond activates a dormant acceptor through a charge induction between phenolic hydrogen and a heteroaryl nitrogen moiety. As a result, a new fluorochrome is produced, and the molecule exhibits a strong fluorescent emission. When the stren… Show more

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Cited by 13 publications
(4 citation statements)
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References 25 publications
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“…Yellow solid; 42 % yield (42 mg); 1 H NMR (400 MHz, CDCl 3 ): δ =15.47 (br s, 1 H), 9.90 (s, 1 H), 8.53 (ddd, J= 5.2, 1.9, 1.0 Hz, 1 H), 8.38 (d, J= 2.1 Hz, 1 H), 8.06 (dt, J= 8.4, 1.1 Hz, 1 H), 7.92 (ddd, J= 8.3, 7.5, 1.8 Hz, 1 H), 7.82 (dd, J= 8.5, 2.0 Hz, 1 H), 7.34 (ddd, J= 7.5, 5.1, 1.1 Hz, 1 H), 7.11 ppm (d, J= 8.5 Hz, 1 H); 13 C NMR (100 MHz, CDCl 3 ): δ =190.7, 166.2, 156.7, 145.7, 138.5, 133.5, 128.6, 128.2, 122.6, 119.5, 119.4, 118.9 ppm; HRMS (ESI): m / z calcd for C 12 H 10 NO 2 : 200.0707 [ M +H] + ; found: 200.0700. The measured NMR data agreed with the literature values …”
Section: Methodssupporting
confidence: 88%
“…Yellow solid; 42 % yield (42 mg); 1 H NMR (400 MHz, CDCl 3 ): δ =15.47 (br s, 1 H), 9.90 (s, 1 H), 8.53 (ddd, J= 5.2, 1.9, 1.0 Hz, 1 H), 8.38 (d, J= 2.1 Hz, 1 H), 8.06 (dt, J= 8.4, 1.1 Hz, 1 H), 7.92 (ddd, J= 8.3, 7.5, 1.8 Hz, 1 H), 7.82 (dd, J= 8.5, 2.0 Hz, 1 H), 7.34 (ddd, J= 7.5, 5.1, 1.1 Hz, 1 H), 7.11 ppm (d, J= 8.5 Hz, 1 H); 13 C NMR (100 MHz, CDCl 3 ): δ =190.7, 166.2, 156.7, 145.7, 138.5, 133.5, 128.6, 128.2, 122.6, 119.5, 119.4, 118.9 ppm; HRMS (ESI): m / z calcd for C 12 H 10 NO 2 : 200.0707 [ M +H] + ; found: 200.0700. The measured NMR data agreed with the literature values …”
Section: Methodssupporting
confidence: 88%
“…The p K a values of the photoacids also affect their applications; thus, the p K a values of the photoacids were measured by using the S‐curve method, which was tested by UV/Vis spectroscopy (Figures S23–S38). The introduction of an EWG (i.e., NO 2 , CF 3 , and CN) and a halogen (i.e., F, Cl, and Br) reduced the p K a values, yet the introduction of an EDG (i.e., OMe) increased the p K a value; this was mainly caused by electronic effects.…”
Section: Resultsmentioning
confidence: 99%
“…In addition, owing to the intramolecular H-bond in HBT-Py,t he phenyla nd BT rings were coplanar in HBT-Py but not in HBT-Py-Me (Figure S4). All of these resultse stablished that an LBHB exists in HBT-Py.T oa ne xtent,t he coplanar structure of HBT-Py also explained its high F f (29 %);n on-radiativee lectron decay was dramatically reduced by locking the excited molecule in ap lanar conformation, [17] whereas the F f of HBT-Py-Me was only 16 %. To further verify the existence of as trong intramolecular Hbond in HBT-Py,i ts fluorescence spectra at different pH values (4)(5)(6)(7)(8)(9)(10)(11)(12) weremeasured.…”
mentioning
confidence: 96%