A theoretical study of a series of novel two-photon nitric oxide (NO) fluorescent probes based on BODIPY. (25th August 2015)

• Record Type: Journal Article
• Authors: Zhang, Li; Zou, Lu-Yi; Guo, Jing-Fu; Wang, Dan; Ren, Ai-Min
• Is Part Of: New journal of chemistry. Volume 39:Number 11(2015:Nov.)
• Page Start: 8342
• Page End: 8355
• Publication Date: 2015-08-25
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c5nj01023c
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : The PET probing mechanism and intrinsic two-photon absorption properties of the studied molecules are rationally explained. Abstract : In this work, a series of novel nitric oxide (NO) probes and the corresponding reaction products are designed based on boron dipyrromethene (BODIPY) and heteroaryl-fused BODIPY or 3, 5-distyryl substituted BODIPY (KFL). Furthermore, the mechanism of recognizing NO controlled by intramolecular photoinduced electron transfer (PET) is verified by theoretical chemistry computation in this work. More importantly, the two-photon absorption properties of these novel chromophores are explored by using DALTON program. The results of our study show that the two-photon absorption cross sections of the designed molecules are as large as 1056.9–39702.5 GM with the wavelengths ranging from 700 to 850 nm, especially for KFLs based on the 3, 5-distyryl substituted BODIPY core, which have more potential for applications in two-photon absorption fluorescence imaging with larger two-photon absorption cross sections in the near-infrared region, because of their better rigidity and π-conjugation that are more conducive to intramolecular charge transfer. Finally, this work presents structure modification strategies for increasing two-photon response. We hope the study can provide helpful information for further investigating two-photon NO probes.