Controllable Versatility in a Single Molecular System from Photoisomerization to Photocyclization

Cyanostilbene is a typical photoresponsive group with multiple photochemical reactions. However, it is still challenging to achieve multiple photochemical reactions and versatility in the same molecular system at one wavelength excitation. The cyanostilbene-based molecule synthesized in this work can undergo photoisomerization and photocyclization in sequence under continuous illumination at 365 nm in solution. This process is demonstrated by nuclear magnetic resonance, high-resolution mass spectroscopies, and single crystal X-ray diffraction. The fluorescence intensity of the solution gradually increases by more than ten times with the extension of the illumination time due to the formation of a photocyclization product with a high fluorescence quantum yield. Based on this interesting phenomenon, the multifunctional applications of this system are presented. This provides a design idea for multifunctional molecules via photochemical reactions. The synthesized cyanostilbene-based molecule can undergo photoisomerization and photocyclization in sequence under continuous illumination at 365 nm in solution. Meanwhile, these reaction processes are usually accompanied by changes in fluorescence properties. The combination of fluorescence enhancement and multicolor fluorescence enables advanced optical information storage and anti-counterfeiting.image

Automated summary

In this study, a cyanostilbene-based molecule was synthesized to achieve multiple photochemical reactions and functionalities in the same molecular system under one wavelength excitation. The molecule can undergo photoisomerization and photocyclization sequentially under continuous illumination at 365 nm in solution, leading to enhanced fluorescence intensity. This research provides a design idea for multifunctional molecules via photochemical reactions.