Multipolar Porphyrin-Triazatruxene Arrays for Two-Photon Fluorescence Cell Imaging.
Chemistry
; 26(61): 13842-13848, 2020 Nov 02.
Article
en En
| MEDLINE
| ID: mdl-32468667
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 (436â
GM) is significantly larger than that of the ZnP reference (59â
GM). The δTPA values of TAT-(ZnP)2 and TAT-(ZnP)3 further increase to 1031 and up to 1496â
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.
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Texto completo:
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Banco de datos:
MEDLINE
Asunto principal:
Porfirinas
/
Carbazoles
/
Microscopía de Fluorescencia por Excitación Multifotónica
Límite:
Humans
Idioma:
En
Año:
2020
Tipo del documento:
Article