Pyrene Derivative Emitting Red or near-Infrared Light with Monomer/Excimer Conversion and Its Application to Ratiometric Detection of Hypochlorite

Abstract

Fluorescent sensors are attractive and versatile tools for both chemical sensing and biological imaging. Herein, a novel pyrene derivative fluorophore, Py-Cy, possessing the monomer/excimer conversion feature, was synthesized; and the design rationale for this fluorophore is combination of extending conjugation length and incorporating donor-π-acceptor structure. The positively charged Py-Cy shows quite good water solubility and exhibits absorption in the visible-light range, and its monomer and excimer emit red light and near-infrared light respectively, which is extremely beneficial for biosensing or bioimaging. To explore the potential utilization of this new fluorophore, we choose hypochlorite as a model analyte, which can break the double bond in the molecular structure, thereby generating the water-insoluble pyrenecarboxaldehyde; this process correspondingly leads to fluorescence changes and thus affords the ratiometric fluorescent detection of hypochlorite in real samples and cell imaging. The approach offers new insights for designing other fluorophores which emit red or near-infrared light and for devising technically simple ratiometric fluorescent sensors.

Exploring organic photosensitizers based on hemicyanine derivatives: a sustainable approach for preparation of amide linkages

“…S40-S44 in ESI †). [12][13][14] Derivative C2 was synthesized by condensation of 1,2,3,3-tetramethyl-3H-indol-1-ium with 2,7-azaindole-3-carboxaldehyde in ethanol (Scheme 2). 15 The structure of C2 was characterized by various spectroscopic and analytical studies ( Fig.…”

N‐Heterocyclic Carbene Boranes as Reactive Oxygen Species‐Responsive Materials: Application to the Two‐Photon Imaging of Hypochlorous Acid in Living Cells and Tissues

“…Although hydroboranes and borohydrides have been among the most popular and selective reducing agents since the 1950s, their sensitivity to aerobic oxidation or hydrolysis has constrained their applications as ROSresponsive materials.The reactivity of hydroboranes is tamed by the formation of adducts with aLewis base. [13,14] Selective oxidative hydrolysis of the BÀHb onds of 1·BH 3 by aq. [10] Furthermore,C urran, Lacôte and co-workers have demonstrated that NHC boranes can perform as either radical [11] or ionic [9,12] reductants.…”

“…Because of its low polarity, 1·BH 3 reversibly forms colloidal aggregates,f acilitating pyrene excimer emission. [13,14] Selective oxidative hydrolysis of the BÀHb onds of 1·BH 3 by aq. HOCl results in the formation of the imidazolium salt 1·H + , which exclusively emits as ad istinct monomeric species.…”

A Nanoprobe for Diagnosing and Mapping Lymphatic Metastasis of Tumor Using 3D Multispectral Optoacoustic Tomography Owing to Aggregation/Deaggregation Induced Spectral Change

“…As a noninvasive imaging method with high sensitivity, pure optical detection/imaging techniques have been employed to detect and visualize various cancers and even detect lymph node metastasis . Nevertheless, based on diffuse‐light‐based imaging, pure optical detection techniques have some limitations such as relatively low spatial resolution and penetration depth because of strong light scattering in deep tissue . On the other hand, optoacoustic (OA) imaging, also known as photoacoustic (PA) imaging, integrates the good contrast and high sensitivity attainable in optical imaging with the deep penetration and high resolution of ultrasound .…”