Aza-BODIPY-based Fluorescent and Colorimetric Sensors and Probes

Abstract

Aza-boron-dipyrromethenes (Aza-BODIPYs) represent an important class of chromophores absorbing and emitting in the near-infrared (NIR) region. They have unique optical and electronic features and higher physiological and photo stability than other NIR dyes. Especially after the development of facile synthetic routes, Aza-BODIPYs have become indispensable fluors that can find various applications ranging from chemosensors, bioimaging, phototherapy, solar energy materials, photocatalysis, photon upconversion, lasers, and optoelectronics. Herein, we review Aza-BODIPY based fluorescent and colorimetric chemosensors. We show the potential and untapped toolbox of Aza-BODIPY based fluorescent and colorimetric chemosensors. Hence, we divide the fluorescent and colorimetric chemosensors and probes into five sections according to the target analytes. The first section begins with the chemosensors developed for pH. Next, we discuss Aza-BODIPY based ion sensors including, metal ions and anions. Finally, we present the chemosensors and probes concerning reactive oxygen (ROS) and nitrogen species (RNS) along with biologically relevant species in the last two sections. We believe that Aza-BODIPYs are still in their infancy, and they have a promising future for translation from the bench to real biomedical and materials science applications. After two decades of intensive research, it seems that there are many more to come in this already fertile field. Overall, we hope that future work will further expand the applications of Aza-BODIPY in many areas.

Near‐Infrared Absorbing Aza‐BODIPY Dyes for Optoelectronic Applications

“…This makes tBu groups substituted aza-BODIPY (tBu-azaBDP 61) a highly desirable photothermal and photodynamic therapy agent.Ring-fused aza-BODIPY dyes have been used as fluorescent probes in the biological systems related to their desirable photophysical characteristics. [85,86] Kobayashi and co-workers synthesized fluorescent probes based on ring-fused aza-BODIPY structures. [18] They investigated the pH dependence on the optical properties of aza-BODIPY 62 in dichloromethane by sequentially adding trifluoroacetic acid (TFA).…”

“…However, their photothermal conversion efficiency and single oxygen generation capability are more effective compared to phenyl based aza‐BODIPY ( Ph ‐ azaBDP 60 ). This makes tBu groups substituted aza‐BODIPY ( tBu ‐ azaBDP 61 ) a highly desirable photothermal and photodynamic therapy agent.Ring‐fused aza‐BODIPY dyes have been used as fluorescent probes in the biological systems related to their desirable photophysical characteristics [85,86] . Kobayashi and co‐workers synthesized fluorescent probes based on ring‐fused aza‐BODIPY structures [18] .…”

A NIR-Fluorochrome for Live Cell Dual Emission and Lifetime Tracking from the First Plasma Membrane Interaction to Subcellular and Extracellular Locales

“…Introduced in the early 2000s, the BF 2 -azadipyrromethenes are an exciting near-infrared (NIR) emissive platform from which application-specific imaging agents can be constructed [ 17 , 18 , 19 ]. They are ideally suited to both live cellular and in vivo imaging, with fluorescence wavelengths tunable within the low-level energy range of 650 to 850 nm, low toxicity, and excellent photo stability [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ].…”

Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline Moiety

“…Boron dipyrromethenes (BODIPYs) and their meso-nitrogen-substituted analogues called aza-BODIPYs have received considerable research attention owing to their fascinating optical properties and potential applications, such as bioimaging [1][2][3][4][5][6][7], chemosensors [8][9][10][11], laser dyes [12], sensitizers for photodynamic [13][14][15] and photothermal therapies [16,17], and optoelectronic materials for light-emitting diodes [18][19][20] and organic photovoltaics [10,21]. Despite their excellent chemical and photophysical properties, the fluorescent emission of most BODIPY derivatives is virtually quenched in the solid state due to the small Stokes shifts and strong intermolecular π-π stacking interactions enhanced by the symmetric, planar structure [22][23][24][25][26].…”