Indoline spiropyrans containing conjugated cationic vinyl-3H-indolium fragment and their analogues with formyl substituent in the 2H-chromene moiety were synthesized by a simple one-pot method. The structure of the obtained compounds was confirmed by 1H and 13C NMR (including 2D methods) and IR spectroscopy, as well as by element analysis and HRMS. Molecular structures of 1,3,3,6´-tetramethyl-8´-formyl-spiro[indoline-2,2´-2H-chromene] 8 and its cationic derivative 5 were refined by single crystal X-ray and compared. Notably, it was found that the crystals of formyl-substituted spiropyran contain both enantiomers (R- and S-) of the molecule in the unit cell. Photochromic properties of all the compounds were studied and compared using spectral-photokinetic methods. It was found out that electron-withdrawing substituents (vinyl-3H-indolium fragment and formyl group) located at the position 6´ of 2H-chromene moiety stabilize merocyanine isomer more effectively, than at the position 8´, leading even to the appearance of negative photochromism for the compound 3 with cationic substituent, which is quite unusual for this class of organic photochromes. Also, it was shown that chlorine atoms as σ-acceptors at the positions 5 and 5´´ of hetarene moiety and cationic fragment can suppress photochromic behavior.