“…These interesting theoretical data strongly encouraged us to investigate the differences of 6- and 7-azaisoquinolinones before using them to construct larger N-containing heteroacenes. In addition, since azaisoquinolinones contain N and O atoms, which are well-known atoms for the coordination with metal ions, we believe that azaisoquinolinones should have some responses to metal ions.…”
Since isoquinolinones and their derivatives have been demonstrated to be powerful building blocks in constructing larger acenes and twistacenes, azaisoquinolinones and their analogues could also be important intermediates to approach larger N-heteroacenes. In this paper, we are interested in developing a concise method to synthesize novel azaisoquinolinones building blocks and studying their physical properties. Our results showed that the different N positions have a large effect on the optical and electrochemical properties of azaisoquinolinones. For example, protonation of 6- and 7-azaisoquinolinones shows different shifts of UV-vis and FL spectra. More interestingly, 6- and 7-azaisoquinolinones exhibited different interactions with metal ions in CH3CN solution. Upon the addition of 2 equiv of Fe(3+), 6-azaisoquinolinone displayed an absorption wavelength red-shifted from 470 to 540 nm (Δλ = 70 nm) with a color change from yellow to red, while the interaction between Fe(3+) and 7-azaisoquinolinone was very weak and there was no obvious color change (Δλ = 18 nm). Moreover, theoretical calculations confirmed the different optical properties with 6- and 7-azaisoquinolinones.
“…These interesting theoretical data strongly encouraged us to investigate the differences of 6- and 7-azaisoquinolinones before using them to construct larger N-containing heteroacenes. In addition, since azaisoquinolinones contain N and O atoms, which are well-known atoms for the coordination with metal ions, we believe that azaisoquinolinones should have some responses to metal ions.…”
Since isoquinolinones and their derivatives have been demonstrated to be powerful building blocks in constructing larger acenes and twistacenes, azaisoquinolinones and their analogues could also be important intermediates to approach larger N-heteroacenes. In this paper, we are interested in developing a concise method to synthesize novel azaisoquinolinones building blocks and studying their physical properties. Our results showed that the different N positions have a large effect on the optical and electrochemical properties of azaisoquinolinones. For example, protonation of 6- and 7-azaisoquinolinones shows different shifts of UV-vis and FL spectra. More interestingly, 6- and 7-azaisoquinolinones exhibited different interactions with metal ions in CH3CN solution. Upon the addition of 2 equiv of Fe(3+), 6-azaisoquinolinone displayed an absorption wavelength red-shifted from 470 to 540 nm (Δλ = 70 nm) with a color change from yellow to red, while the interaction between Fe(3+) and 7-azaisoquinolinone was very weak and there was no obvious color change (Δλ = 18 nm). Moreover, theoretical calculations confirmed the different optical properties with 6- and 7-azaisoquinolinones.
“…Sb was determined from the emission intensity of the sensor solution in the absence of metal ions by performing a series of five measurements. The detection limit was calculated from the calibration plot and the values are collected in Table 3 [72,73]. The detection limit for complexes 1-4 was found to be in the range of 1.2 × 10 -6 -4.3 × 10 -6 M. The detection limit for complex 1 (4.3 × 10 -6 M) was higher compared to complex 4 (1.2 × 10 -6 M),…”
“…Both Fe 3+ and Cu 2+ ions play significant role in biological processes such as muscle contraction, enzymatic catalysis and nerve conduction . Copper is one of the essential trace elements in our biological systems and acts as cofactor in various metalloenzymes such as tyrosinase, cytochrome co‐oxidase and superoxide dismutase . However, the excess accumulation of copper in human body can cause bone disorders, and serious neurodegenerative diseases like Menke's, Alzheimer's and Parkinson's diseases .…”
A new isatin‐triazole tethered rhodamine based fluorescent probe R1 (1‐(2’’‐(4’‐(((3’’’,6’’’‐bis(diethylamino)‐3’’‐oxospiro[isoindoline‐1’’,9’’’‐xanthen]‐2’’‐yl)amino)methyl)‐1H‐1’,2’,3’‐triazolyl)ethyl)indoline‐2,3‐dione) has been synthesized using click chemistry approach. Probe R1 exhibits a dual sensor property for Cu2+ and Fe3+ ions through turn‐on fluorescence response. A prominent colour change from colourless to pink allows the naked eye identification of aforementioned metal ions. R1 forms a 1:2 complex with Cu2+ and Fe3+ ions with binding constants 8.0 × 108 and 2.93 × 107 M−2, respectively. The binding mode is scrutinised through various spectroscopic techniques which is further supported by theoretical calculations. The detection limit of R1 for Cu2+ and Fe3+ ions is found to be 12.2 nM and 0.33 μM, respectively. Further, R1 has been evaluated for its potential to detect Cu2+ ions in biological systems using fluorescence cell imaging studies.
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