Title

Near-Infrared-Emitting Squaraine Dyes With High 2Pa Cross-Sections For Multiphoton Fluorescence Imaging

Keywords

and two-photon fluorescence microscopy; bioimaging; linear and nonlinear optical properties; near infrared (NIR) dyes; squaraine

Abstract

Designed to achieve high two-photon absorptivity, new near-infrared (NIR) emitting squaraine dyes, (E)-2-(1-(2-(2-methoxyethoxy)ethyl)-5-(3,4,5- trimethoxystyryl)-1H-pyrrol-2-yl)-4-(1-(2-(2-methoxyethoxy)ethyl)-5-(3,4, 5-trimethoxystyryl)-2H-pyrrolium-2-ylidene)-3-oxocyclobut-1-enolate (1) and (Z)-2-(4-(dibutylamino)-2-hydroxyphenyl)-4-(4-(dibutyliminio) -2-hydroxycyclohexa-2,5-dienylidene)-3-oxocyclobut-1-enolate (2), were synthesized and characterized. Their linear photophysical properties were investigated via UV-visible absorption spectroscopy and fluorescence spectroscopy in various solvents, while their nonlinear photophysical properties were investigated using a combination of two-photon induced fluorescence and open aperture z-scan methods. Squaraine 1 exhibited a high two-photon absorption (2PA) cross-section ( 2PA), ∼20-000 GM at 800 nm, and high photostability with the photochemical decomposition quantum yield one order of magnitude lower than Cy 5, a commercially available pentamethine cyanine NIR dye. The cytotoxicity of the squaraine dyes were evaluated in HCT 116 and COS 7 cell lines to assess the potential of these probes for biomedical imaging. The viability of both cell lines was maintained above 80% at dye concentrations up to 30 μM, indicating good biocompatibility of the probes. Finally, one-photon fluorescence microscopy (1PFM) and two-photon fluorescence microscopy (2PFM) imaging was accomplished after incubation of micelle-encapsulated squaraine probes with HCT 116 and COS 7 cells, demonstrating their potential in 2PFM bioimaging. © 2012 American Chemical Society.

Publication Date

6-27-2012

Publication Title

ACS Applied Materials and Interfaces

Volume

4

Issue

6

Number of Pages

2847-2854

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1021/am300467w

Socpus ID

84863214383 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/84863214383

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