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Multipolar Porphyrin‐Triazatruxene Arrays for Two‐Photon Fluorescence Cell Imaging
Author(s) -
Zhang Jinghui,
Gong Lei,
Zhang Xiaoshuang,
Zhu Mengliang,
Su Chaorui,
Ma Qing,
Qi Dongdong,
Bian Yongzhong,
Du Hongwu,
Jiang Jianzhuang
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001367
Subject(s) - fluorescence , conjugated system , porphyrin , biocompatibility , molecule , two photon excitation microscopy , photochemistry , absorption (acoustics) , chemistry , excited state , materials science , optics , polymer , atomic physics , physics , organic chemistry , composite material
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.