Dicyanopyridine derivatives: One-pot preparation, ACQ-to-AIE transformation, light-conversion quality and photostability

Abstract

Low cost and strong fluorescence emission are two important guarantees for luminogens used as light conversion agents. By one-pot multicomponent approach and inexpensive starting materials, three dicyanopyridine (DP) derivatives named as DCP (2-amino-6-methoxy-4-phenylpyridine-3,5-dicarbonitrile), DCO (2-amino-6-methoxy-4-(4-methoxyphenyl) pyridine-3,5-dicarbonitrile) and DCC (2-amino-4-(4-cyanophenyl)-6-methoxypyridine-3,5-dicarbonitrile) were designed and synthesized.Meanwhile, the ACQ-to-AIE transformation was successfully realized by altering substituent groups rather than traditional rotor–stator theory. Based on crystal analysis and theoretical calculations, the ACQ-to-AIE transformation is attributed to the tunable stacking modes and intermolecular weak interactions. Owing to matched fluorescence emission, low lost, high yield, and AIE activity, DCC is used as light conversion agents and doped in EVA matrix. The light conversion quality confirms that DCC can not only convert ultraviolet light, but also significantly improve the transmittance of 25 %/40 % EVA, whose photosynthetic photon flux density at 400–500 nm and 600–700 nm increased to 30.67 %/30.21 % and 25.37 %/37.82 % of the blank film, respectively. After 20 h of UV irradiation (365 nm, 40 W), the fluorescence intensities of DCC films can maintain 92 % of the initial values, indicating good photostability in the doping films. This work not only provides an excellent and low-cost light conversion agent, but also has important significance for ACQ-to-AIE transformation of luminogens.