Internal C–C Bond Rotation in Photoisomers of α‐Bisimines: a Light‐Responsive Two‐Step Molecular Speed Regulator Based on Double Imine Photoswitching

Abstract

Abstract:Benzil-based α-bisimines are implemented as photoswitches for the construction of a speed-regulating molecular device, in which, by application of light, three different states may be addressed, showing distinct frequencies of internal C-C

Photoswitchable block copolymers based on main chain α-bisimines

“…42 On the other hand, imines, especially chiral aromatic (e.g., benzil) imines, have been recognized as potential candidates for molecular motors due to their photo-driven E/Z isomerization characteristic. 43,44 Whereas the light-induced E/Z isomerization of imines has been known for almost 70 years, 45 this light-responsive feature has yet to be exploited in polymer science. In fact, there are only very few examples for the utilization of light-responsive imines in polymer science.…”

TEMPO mediated oxidative annulation of aryl methyl ketones with amines/ammonium acetate for imidazole synthesis

“…For example, 1H-imidazole 3a underwent 5-bromination and subsequent Sonogashira coupling to give a more functionalized compound 6 in a high yield (Scheme 2(2)). [1][2][3][4][5][6][7][8][9][10][11][12][14][15][16][17][18][19][20][21] The above results demonstrated the practicality of this protocol.…”

“…Although there is no report on the synthesis of dibenzyl-1phenylethane-1,2-diimine (C), we treated 2-oxo-2-phenylacetaldehyde (8) with benzylamine (2a) for the in situ synthesis of it according to the synthetic method of its analogue 12. 20 Then, the addition of TEMPO and NaIO 4 gave the desired product (3a) in 40% yield (Scheme 3( 8)). This result suggested that diimine C was the reaction intermediate.…”

Wavelength-selective light-matter interactions in polymer science

“…This limits their utility in wavelength-selective photochemistry and presents an opportunity for the development of novel synthetic a-bisimine derivatives. 47 Indigo dyes were first identified by Mostoslavskii in 1961 (Figure 4D), 33 and are attractive for their low-energy visible light photoisomerization and excellent photostability. For example, hemiindigo dyes (X = N, Figure 4D) with electron-rich aromatic substituents can be photoswitched with yellow-to-red light ($593-633 nm) for both isomers.…”