Multipolar Porphyrin‐Triazatruxene Arrays for Two‐Photon Fluorescence Cell Imaging. Issue 61 (28th September 2020)

• Record Type: Journal Article
• Authors: Zhang, Jinghui; Gong, Lei; Zhang, Xiaoshuang; Zhu, Mengliang; Su, Chaorui; Ma, Qing; Qi, Dongdong; Bian, Yongzhong; Du, Hongwu; Jiang, Jianzhuang
• Is Part Of: Chemistry. Volume 26:Issue 61(2020)
• Page Start: 13842
• Page End: 13848
• Publication Date: 2020-09-28
• Subjects: cell imaging -- porphyrin -- triazatruxene -- two-photon absorption -- two-photon excited fluorescence; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202001367
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Two‐photon excited fluorescent (TPEF) materials are highly desirable for bioimaging applications owing to their unique characteristics of deep‐tissue penetration and high spatiotemporal resolution. Herein, by connecting one, two, or three electron‐deficient zinc porphyrin units to an electron‐rich triazatruxene core via ethynyl π‐bridges, conjugated multipolar molecules TAT‐(ZnP) n ( n =1–3) were developed as TPEF materials for cell imaging. The three new dyes present high fluorescence quantum yields (0.40–0.47) and rationally improved two‐photon absorption (TPA) properties. In particular, the peak TPA cross section of TAT‐ZnP (436 GM) is significantly larger than that of the ZnP reference (59 GM). The δ TPA values of TAT‐(ZnP)2 and TAT‐(ZnP)3 further increase to 1031 and up to 1496 GM, respectively, indicating the effect of incorporated ZnP units on the TPA properties. The substantial improvement of the TPEF properties is attributed to the formation of π‐conjugated quadrapole/octupole molecules and the extension of D ‐π‐A‐D systems, which has been rationalized by density function theory (DFT) calculations. Moreover, all of the three new dyes display good biocompatibility and preferential targeting ability toward cytomembrane, thus can be superior candidates for TPEF imaging of living cells. Overall, this work demonstrated a promising strategy for the development of porphyrin‐based TPEF materials by the construction and extension of D ‐π‐A‐D multipolar array. Abstract : Living image : Conjugated multipolar porphyrin‐triazatruxene arrays, exhibiting large two‐photon fluorescence (TPA) cross‐sections and high fluorescence quantum yields, were successfully applied for TPEF cell imaging.