Properties and Exciting Facts About 9H-Pyrido[2,3-b]indole

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In cyclohexane as the solvent, 1-azacarbazole (or alpha-carboline) (AC) forms fluorescent ground state 1:1 hydrogen-bonded complexes with N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA) and hexamethylphosphoramide (HMPA). The absorption and fluorescence spectra of the complexes are red shifted with respect to those of the non-bonded AC, and their association constants increase as the hydrogen-bonding acceptor properties of the amides increase. Fluorescence of the AC-DMF and AC-DMA solutions show monoexponential or biexponential decays depending on the monitored emission wavelength. To aid the interpretation of these results, we have also studied the effect that triethylamine and methylethylketone addition produces on the absorption and fluorescence spectra of AC. Triethylamine does not significantly affect the absorption spectrum of AC, but it dynamically quenches its fluorescence. Conversely, methylethylketone behaves similarly as amides do. On the basis of the above results, we assume that, in the ground state, the hydrogen-bonding interaction takes place between the pyrrolic NH group of AC and the carbonyl group of the amide. Hydrogen bonded complexes and non-bonded AC behave in the singlet excited state as independent fluorophores. Singlet excited state of free AC is dynamically quenched by DMF and DMA. The quenching mechanism involves the hydrogen-bonding interaction of the pyrrolic NH group of AC and the lone electron pair of the amide nitrogen atom. For HMPA, probably due to geometrical restrictions, this quenching process is absent.

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Reference：
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles