Polycyclic aromatic hydrocarbons (PAHs) with boron–nitrogen (BN) moieties have attracted tremendous interest due to their intriguing electronic and optoelectronic properties. However, most of the BN-fused π-systems reported to date are difficult to modify and exhibit traditional aggregation-caused quenching (ACQ) characteristics. This phenomenon greatly limits their scope of application. Thus, continuing efforts to seek novel, structurally distinct and functionally diverse structures are highly desirable. Herein, we proposed a one-stone-two-birds strategy including simultaneous exploration of reactivity and tuning of the optical and electronic properties for BN-containing π-skeletons through flexible regioselective functionalization engineering. In this way, three novel functionalized BN luminogens (DPA-BN-BFT, MeO-DPA-BN-BFT and DMA-DPA-BN-BFT) with similar structures were obtained. Intriguingly, DPA-BN-BFT, MeO-DPA-BN-BFT and DMA-DPA-BN-BFT exhibit completely different emission behaviors. Fluorogens DPA-BN-BFT and MeO-DPA-BN-BFT exhibit a typical ACQ effect; in sharp contrast, DMA-DPA-BN-BFT possesses a prominent aggregation induced emission (AIE) effect. To the best of our knowledge, this is the first report to integrate ACQ and AIE properties into one BN aromatic backbone with subtle modified structures. Comprehensive analysis of the crystal structure and theoretical calculations reveal that relatively large twisting angles, multiple intermolecular interactions and tight crystal packing modes endow DMA-DPA-BN-BFT with strong AIE behavior. More importantly, cell imaging demonstrated that luminescent materials DPA-BN-BFT and DMA-DPA-BN-BFT can highly selectively and sensitively detect lipid droplets (LDs) in living MCF-7 cells. Overall, this work provides a new viewpoint of the rational design and synthesis of advanced BN–polycyclic aromatics with AIE features and triggers the discovery of new functions and properties of azaborine chemistry.

The development of smart materials, in particular those exhibiting highly sensitive mechanochromic luminescence (MCL) is desirable, but challenging since the MCL internal mechanism and the structure–performance relationship still remain unclear. Herein, we report a new MCL material, BN benzo[f]tetraphene, synthesized using a molecular-level design strategy by introducing a BN unit to a π-conjugated system. By investigating BN benzo[f]tetraphene (5) and its analogue, it was found that the introduction of the boron-nitrogen unit is the key to tailoring the molecular dipole moment and intermolecular interactions, which can therefore form an easily deformable molecular stacking pattern and endow 5 with wonderful MCL properties. Theoretical calculations confirmed that inherent energies like excited singlet (S) and highly sensitive triplet (T) states exist in the MCL process, and the formation and fracture of ordered molecular aggregates have significant effect on radiative and nonradiative transitions. The material also shows high-contrast and self-reversible properties related to thermal-and force-stimulus, which makes it a promising candidate for security ink, optical recording applications. This work possibly opens up a new way to develop efficient organic smart materials, and therefore, trigger the discovery of new functions and properties of azaborine compounds.

In this study, the total polyphenol content (TPC), total flavonoid content (TFC), and biological activity of yam polyphenols (including free phenolics, conjugated phenolics, and bound phenolics) were investigated during home cooking. Polyphenol components were preliminary detected in raw yam by HPLC, including 2, 4-dihydroxybenzoic acid, syringic acid, vanillic acid, 4-coumaric acid, and sinapic acid. TPC and TFC of soluble conjugated polyphenols were the main phenolic compounds in Ruichang yam. Compared with uncooked yam, cooking times of 80 min and 40 min increased the TPC and TFC of multiple types of polyphenols, while cooking reduced the TPC and TFC of AHP (acid-hydrolyzed soluble conjugated polyphenols). All yam polyphenols exhibited good α-Glucosidase inhibitory activity; α-Glucosidase inhibitory activity was significantly higher for a cooking time of 120 min. Only some types of polyphenols had lower pancreatic lipase half-inhibition concentrations than orlistat when cooked. The pancreatic lipase of FPs (free polyphenols), BHPs (alkali-hydrolyzed soluble conjugated polyphenols), and ABPs (acid-hydrolyzed insoluble bound polyphenols) was the stronges when cooking for 80 min, and the pancreatic lipase inhibitory activity of AHPs and BBPs (alkali-hydrolyzed insoluble bound polyphenols) was strongest when cooking for 40 min. Pearson’s correlation coefficient analysis revealed that the TPC was positively correlated with the TFC, the IC₅₀ value of α-Glucosidase was negatively correlated with the IC₅₀ value of pancreatic lipase, and redox activity was positively correlated with the TPC and TFC, respectively.

The antioxidant properties of butterfly pea flower (BF), which is rich in natural anthocyanins, have garnered significant attention. The impact of digestion and metabolism on BF extracts and evaluate their subsequent antioxidant activities in vivo were explored in the present study. After in vitro digestion, 42.03 ± 2.74% of total anthocyanins from BF extracts remained, indicating a negative influence of the digestion process on the bioaccessibility of phenolic compounds derived from BF. Furthermore, UPLC-LTQ-Orbitrap-MS² analysis identified a total of four prototypes and twenty-seven metabolites in rat plasma or urine samples following the intake of BF extracts. The kinetics of key metabolites including delphinidin 3-glucoside (D3G), cyanidin-3-glucoside (C3G), and 4-hydroxybenzoic acid were subsequently determined in blood, and the Cmax values were 69.034 ± 8.05 nM and 51.65 ± 3.205 nM. These key metabolites derived from BF anthocyanins, including C3G and D3G, and flavonoid quercetin exhibited main antioxidant attributes that improved the plasmic and hepatic activities of various antioxidant enzymes and the total antioxidant capacity (T-AOC) and malondialdehyde (MDA) in a D-galactose-induced rat model. These findings provide insights into the bioaccessibility and bioavailability of bioactive constitutes derived from BF extracts, which are crucial for determining the actual efficacy of BF as well as developing functional foods based on BF.