Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Chemical Science called Molecular engineering enabling reversible transformation between helical and planar conformations by cyclization of alkynes, Author is Yan, Lipeng; Ma, Weixin; Lan, Jingbo; Cheng, Hu; Bin, Zhengyang; Wu, Di; You, Jingsong, which mentions a compound: 1008-89-5, SMILESS is C1(C2=CC=CC=C2)=NC=CC=C1, Molecular C11H9N, Related Products of 1008-89-5.
Mol. engineering enabling reversible transformation between helical and planar conformations was described herein. Starting from easily available 2-(pyridin-2-yl)anilines and alkynes, a one-pot strategy was set up for the synthesis of aza[4]helicenes via two successive rhodium-catalyzed C-H activation/cyclizations. Helical pyrrolophenanthridiziniums was transformed into planar conformations through the cleavage of acidic pyrrole N-H, leading to turn-off fluorescence. NMR spectra, single crystal X-ray diffraction and DFT calculations demonstrated that the formation of an intramol. C-H···N hydrogen bond was beneficial to stabilize the pyrrole nitrogen anion of the planar mol. and provided increased planarity. The reversible conformation transformations was finely adjusted by the electron-donating and -withdrawing groups on the π+-fused pyrrole skeleton in the physiol. pH range, thus affording an opportunity for pH-controlled intracellular selective fluorescence imaging. Pyrrolophenanthridiziniums show turn-on fluorescence in lysosomes owing to the acidic environment of lysosomes and turn-off fluorescence out of lysosomes, indicating the occurrence of the deprotonation reaction outside lysosomes and the corresponding transformation from helical to planar conformations.
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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