Zhiquan Li,Xiucheng Zou,Guigang Zhu,Xiaoya Liu,Ren Liu
Developing efficient unimolecular visible light-emitting diode (LED) light photoinitiators (PIs) with photobleaching capability, which are essential for various biomedical applications and photopolymerization of thick materials, remains a great challenge. Herein, we demonstrate the synthesis of a series of novel PIs, containing coumarin moieties as chromophores and oxime ester groups as initiation functionalities and explore their structure–activity relationship. The investigated oxime esters can effectively induce acrylates and thiol-based click photopolymerization under 450 nm visible LED light irradiation. The initiator O-3 exhibited excellent photobleaching capability and enabled photopolymerization of thick materials (∼4.8 mm). The efficient unimolecular photobleachable initiators show great potential in dental materials and 3D printings.
In search of novel natural product-based bioactive molecules, twenty (ten pairs) novel ( Z )-/( E )-anisaldehyde-based oxime ester compounds were designed and synthesized by using anisaldehyde as starting material. Structural characterization of the target compounds was carried out by NMR, FT-IR, ESI-MS, and elemental analysis. Their herbicidal and antifungal activities were preliminarily tested. As a result, at 50 μg/mL, compound ( E )- 5b exhibited excellent to good inhibition rates of 92.3 %, 79.2 %, and 73.9 %, against Rhizoctonia solani , Fusarium oxysporum f. sp. cucumerinum , and Bipolaris maydis , respectively, better than or comparable to that of the positive control chlorothalonil. In addition, at 100 μg/mL, compounds ( E )- 5b , ( E )- 5f , ( Z )- 5f and ( E )- 5d exhibited excellent to good inhibition rates of 85.8 %, 82.9 %, 78.6 % and 64.2 %, respectively, against the root-growth of rape ( B. campestris ), much better than that of the positive control flumioxazin. The bioassay result also showed that the synthesized compounds had obvious differences in antifungal and herbicidal activities between ( Z )- and ( E )-isomers. Preliminary structure–activity relationship was also discussed by theoretical calculation. Graphical
An efficient visible-light-mediated tandem reaction of acryloylbenzamides with alkylboronic acids, arylsulfonyl hydrazides and oxime esters has been developed. The reaction proceeds via radical addition and cyclization to give various isoquinoline-1,3(2H,4H)-diones in satisfactory yields under mild conditions, which provides a good opportunity to discover new meaningful bioactive compounds.
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