Methine Dyes and Pigments

Berneth, Horst

doi:10.1002/14356007.a16_487.pub2

Cited by 9 publications

(6 citation statements)

References 403 publications

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“…A notable drawback for the parent cyanine dyes is that its emission peak l em is closely positioned to its absorption l max , thereby leading to small Stokes shift (typically about 20-50 nm). 9 2-(2¢-Hydroxyphenyl)benzoxazole (HBO) molecule 1 represents another interesting system, which exhibits a large Stokes shift (about 150 nm) arising from the excited-state intramolecular proton transfer (ESIPT). 10 The unique feature of HBO has led to its useful application as a probe molecule in biological systems.…”

Section: Introductionmentioning

confidence: 99%

Zn2+-triggered excited-state intramolecular proton transfer: a sensitive probe with near-infrared emission from bis(benzoxazole) derivative

Pang

2011

Dalton Trans.

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Near-infrared (NIR) emission can offer distinct advantages for biological applications. A fluorescent sensor, Zinhbo-1, based on bis(benzoxazole) ligand with 2,2'-dipicolylamine (DPA) as receptor, was synthesized. In aqueous solution, Zinhbo-1 demonstrates high sensitivity and selectivity for sensing Zn(2+) with about 10-fold enhancement and nanomolar sensitivity (K(d) = 0.29 nM). Moreover, sensor Zinhbo-1 can detect Zn(2+) in near-infrared region (over 700 nm) with large Stokes shift (ca. 230 nm) attributing to the Zn(2+)-induced excited state intramolecular proton transfer (ESIPT).

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Section: Introductionmentioning

confidence: 99%

Zn2+-triggered excited-state intramolecular proton transfer: a sensitive probe with near-infrared emission from bis(benzoxazole) derivative

Pang

2011

Dalton Trans.

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“…Cyanine dyes are the most commonly used NIR fluorescent dyes for bioapplications. 4 As aforementioned, the regulation of the cyanine fluorescence by a PET mechanism is difficult via the Rehm−Weller equation. By contrast, the traditional 7-hydroxycoumarins feature a hydroxyl group, which may be readily modified to tune their optical profiles.…”

Section: Biological Applications Of Cybx Dyesmentioning

confidence: 99%

“…Heptamethinecyanines are desirable for biological imaging applications in living systems due to their NIR absorption and emission properties . Many cyanine-based NIR fluorescent sensors have been engineered, a few of which are operated by the PET mechanism. , However, quenching the fluorescence of cyanines by the PET mechanism is very difficult because of their relatively high-lying occupied molecular orbital energy levels.…”

Section: Integration Of Rhodamine With Cyanine Dyesmentioning

confidence: 99%

“…The oft-used NIR dyes are largely limited to a few traditional NIR fluorophores, such as cyanines, squaraines, and bodipy derivatives. 4 However, these dyes generally have no optically available tunable groups, rending them often favorable as simple fluorescent tags for biospecies but not as the platforms for developing targetsensitive fluorescent sensors. To address this problem, several strategies have been formulated.…”

Section: Introductionmentioning

confidence: 99%

“…Currently, employment of NIR dyes to construct fluorescent sensors for in vivo imaging has made significant progress; however, it is still far from reaching full potential. The oft-used NIR dyes are largely limited to a few traditional NIR fluorophores, such as cyanines, squaraines, and bodipy derivatives . However, these dyes generally have no optically available tunable groups, rending them often favorable as simple fluorescent tags for biospecies but not as the platforms for developing target-sensitive fluorescent sensors.…”

Section: Introductionmentioning

confidence: 99%

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A Unique “Integration” Strategy for the Rational Design of Optically Tunable Near-Infrared Fluorophores

et al. 2017

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Fluorescence imaging is a rapidly growing technique for noninvasive imaging of biological molecules and processes with high spatial and temporal resolution. For effective biological imaging, it is essential and important to develop robust fluorescent dyes, in particular, near-infrared (NIR) fluorescent dyes with favorable optical properties. Compared with the visible light emitting dyes, NIR dyes have relatively longer emission wavelengths (650-900 nm) with lower energy and are advantageous as imaging agents owing to the minimum photodamage of NIR light to biological samples, deep penetration into tissues, and low interference from autofluorescence of biomolecules. Although great efforts have been devoted to engineer NIR fluorophores, it is still very challenging to regulate their photophysical properties as they often lack optically tunable mechanisms, and this shortcoming considerably restricts the realization of their full potential. Consequently, the rational design of small-molecule optically tunable NIR fluorophores is of high priority and great value. In general, two key characteristics are indispensable for designing excellent optically tunable NIR fluorescent dyes. First, NIR fluorescent dyes should display the maximal absorption and emission located in the NIR region and also have the prominent properties including excellent fluorescence quantum yields, large Stokes shifts, good chemical stability and photostability, low cytotoxicity, and desirable compatibility with biological systems. Second, in principle, functional NIR dyes should also possess optically tunable groups, which can be easily modified to afford responsive sites for the targets of interest. With these considerations in mind, in this Account, we described a unique "integration" strategy for judicious design of the optically tunable NIR fluorophores, which are an intuitive combination of the traditional NIR dyes and the optically tunable mechanisms in the visible light emissive dyes. Thus, the versatile strategy may allow not only retention of the NIR emission properties of NIR dyes but also inheritance of the optically tunable mechanisms from the visible light emissive dyes. By the unique integration strategy, a built-in optically tunable group is strategically installed into the traditional NIR fluorescent dyes to directly tune their optical properties. Herein, we present a concise review of the rational design strategy and biological applications of small-molecule optically tunable NIR fluorescent dyes via the unique integration strategy, and we focused mainly on our work and some representative examples from other groups based on our NIR platforms. This Account includes the detailed integration strategy of each class of the NIR fluorescent dyes, the development of their derivatives, and their imaging applications in living systems.

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Azo‐MICs: Redox‐Active Mesoionic Carbene Ligands Derived from Azoimidazolium Dyes

et al. 2019

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Methine Dyes and Pigments

Abstract: The article contains sections titled: 1. Introduction 2. History … Show more

Cited by 9 publications

References 403 publications

Zn2+-triggered excited-state intramolecular proton transfer: a sensitive probe with near-infrared emission from bis(benzoxazole) derivative

Zn2+-triggered excited-state intramolecular proton transfer: a sensitive probe with near-infrared emission from bis(benzoxazole) derivative

A Unique “Integration” Strategy for the Rational Design of Optically Tunable Near-Infrared Fluorophores

Azo‐MICs: Redox‐Active Mesoionic Carbene Ligands Derived from Azoimidazolium Dyes

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