Colorimetric and fluorescence turn-on sensor for biologically important anions based on carbazole derivative

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A colorimetric and fluorescent anion chemosensor containing carbazole group has been designed and synthesized based on photoinduced electron transfer (PET). The strong basic anions such as F − , AcO − and H 2 PO 4 − resulted in significant red-shift in absorption band and enhancement in fluorescent emission intensity of the compound 1 , synchronously accompanied by a “naked eye” color change from light yellow to orange-yellow in organic medium. The determination limit of sensor 1 toward H 2 PO 4 − is 1.0 × 10 − 6 mol·L − 1 . 1 H NMR titration experiments shed light on the nature of the interaction between 1 and the anions. Theoretical investigation further illustrated the possible binding mode of host–guest and the roles of molecular frontier orbitals in anion binding. A colorimetric and fluorescent anion chemosensor based on carbazole derivative has been designed and synthesized based on photoinduced electron transfer (PET). The strong basic anions such as F - , AcO - and H 2 PO 4 - resulted in significant red-shift in absorption band and increase in fluorescent emission intensity of the compound, synchronously accompanied by a “naked eye” color change from light yellow to orange-yellow in organic medium. The determination limit of sensor 1 toward H 2 PO 4 − is 1.0 × 10 − 6 mol·L − 1 . Theoretical investigation further illustrated the possible binding mode of host–guest and the roles of molecular frontier orbitals in anion binding. ► Colorimetric and fluorescence turn-on sensor based on carbazole derivative. ► The interacted mechanism based on photoinduced electron transfer (PET). ► The red-shift in absorption band and increase in emission intensity for H 2 PO 4 − . ► The determination limit of the sensor toward H 2 PO 4 − is 1.0 × 10 − 6 mol·L − 1 . ► The roles of molecular frontier orbitals in anion binding.