Li Ziyong, Ma Xiaoxie, Song Jinzhao, Wang Qilian, Feng Yongliang, Liu Haining, Zhang Pei, Guo Hui, Yin Jun
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, College of Chemistry and Chemical Engineering, Department of Life Science, Luoyang Normal University Luoyang 471934 P. R. China
National Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University Wuhan 430079 P. R. China
Chem Sci. 2024 Dec 18;16(4):1762-1771. doi: 10.1039/d4sc05473c. eCollection 2025 Jan 22.
Developing dithienylethene (DTE)-based fluorescence switches triggered by biocompatible visible light has always been a long-term goal in view of their potential in numerous biological scenarios. However, their practical availability is severely limited by the short visible light (generally less than 500 nm) required for photocyclization, their inability to achieve red or near-infrared emission, and their short fluorescence lifetimes. Herein, we present a novel DTE derivative featuring a dimethylamine-functionalized BF-curcuminoid moiety (NBDC) by using an "acceptor synergistic conjugation system" strategy. The dimethylamine group not only enables a red shift in the absorption and emission wavelengths of the open isomer but also endows NBDC with unique acid/base-gated photochromism. As expected, as-prepared NBDC presents 570 nm/770 nm light-driven photochromic properties, red-emissive fluorescence, and thermally activated delayed fluorescence (TADF) switching in toluene. To our knowledge, this represents the first instance of a yellow-green- and NIR light-controlled red fluorescence DTE switch with the longer fluorescence lifetime. Specifically, NBDC, which shows weak photochromic activity in CHCl, demonstrates enhanced photochromic performance when gated by TFA/TEA. Ultimately, this non-toxic deep-red fluorescence switch has been successfully applied for photoswitchable imaging of living cells and zebrafish, further proving its versatility in life sciences.
鉴于二噻吩乙烯(DTE)基荧光开关在众多生物场景中的潜力,开发由生物相容性可见光触发的此类开关一直是一个长期目标。然而,它们的实际可用性受到光环化所需的短可见光(通常小于500 nm)、无法实现红色或近红外发射以及荧光寿命短的严重限制。在此,我们通过使用“受体协同共轭体系”策略,展示了一种具有二甲胺功能化BF - 姜黄素类部分(NBDC)的新型DTE衍生物。二甲胺基团不仅使开环异构体的吸收和发射波长发生红移,还赋予NBDC独特的酸碱门控光致变色特性。正如预期的那样,所制备的NBDC在甲苯中呈现出570 nm/770 nm光驱动的光致变色特性、红色发射荧光以及热激活延迟荧光(TADF)开关特性。据我们所知,这代表了首例具有较长荧光寿命的黄绿和近红外光控红色荧光DTE开关。具体而言,在CHCl中显示出弱光致变色活性的NBDC,在由三氟乙酸/三乙胺门控时表现出增强的光致变色性能。最终,这种无毒的深红色荧光开关已成功应用于活细胞和斑马鱼的光开关成像,进一步证明了其在生命科学中的多功能性。