BODIPY (boron dipyrromethene) dyes are unique materials with spectroscopic and electrochemical properties comparable to those of aromatic hydrocarbons. Electrochemical studies are useful in understanding the redox properties of these materials and finding structure-stability relations for the radical ions; along with spectroscopy, these studies help researchers design novel compounds with desired properties. This Account represents our attempt at a full description of the electrochemical and electrogenerated chemiluminescence (ECL) properties of the BODIPY dyes. When the dyes are completely substituted with alkyl or other groups, the radical ions of BODIPY dyes are highly stable. But if they include unsubstituted positions, the radical ions can undergo dimerization or other reactions. BODIPY dyes also show unusually large separations, ~1.0 V, between the first and second cyclic voltammetric (CV) waves for both oxidation and reduction half-reactions. Alkyl-substituted BODIPY dyes show good photoluminescence (PL) quantum efficiencies, and radical ion electron transfer annihilation in these molecules produces electrogenerated chemiluminescence (ECL), the intensity of which depends on the structure of the dye. The large separation between waves and the presence of strong ECL signals are both important in the design of stable ECL-based materials. The ECL spectra provide a fast method of monitoring the electrochemical formation of dimers and aggregates from the monomers. BODIPY dyes are particularly good systems for studying stepwise electron transfer in their chemically synthesized oligomers and polymers because of the small separation between the first oxidation and first reduction waves, generally about 2.0-2.4 V, and their relative ease of reduction compared with many other aromatic compounds. The larger separation between consecutive waves for oxidation compared with reduction is noticeable for all BODIPY dimers and trimers. We also observe a more difficult addition or extraction of a third electron compared with the second for the trimers, signaling the importance of electrostatic interactions. In general, BODIPY dyes combine interesting electrochemical and spectroscopic properties that suggest useful analytical applications.

Electrochemistry and electrogenerated chemiluminescence of BODIPY dyes

Electrofluorochromism deals with electrochemical monitoring of luminescence features There are several reasons to be interested in that field The first one is the design of displays working in a similar way to electrochromic devices, substituting colors due to absorption with colors due to emission, thus producing much higher brilliance This requires designing smart molecules and materials, which are likely to exhibit reversible switch of emission by controlling their redox state There are also a lot of analytical applications, especially in biochemical issues, where in situ dual detection of electrochemical and fluorescence signals can lead to very sensitive and selective biosensors To achieve this goal, instrumental developments are necessary, involving, among others, beyond diffraction limit and single molecule detection optical techniques This paper reviews the most recent developments in the above mentioned fields of fluorescence spectroelectrochemistry, coupled detection of fluorescence and electrochemical signals and design of molecules and materials exhibiting electrofluorochromic properties The first part describes the required features for molecular systems to exhibit a reversible switch in their luminescence properties according to a change in their redox state Examples among organic and organometallic dyes and redox labelled fluorophores are listed The second part focuses on the instrumental development in fluorescence spectroelectrochemistry and recent coupling of electrochemical techniques with fluorescence microscopy Finally, some applications and devices are presented in the last part of this review This should give an overview of this emerging research field at the interface between physics, chemistry and biology

Electrofluorochromism: from molecular systems to set-up and display

Modulation of luminescent color or intensity by varying external stimuli, such as temperature, light, ion concentration, etc., has received increasing attention recently because of numerous applications such as sensors, bioanalysis, optical imaging and memories. For instance, electrically induced luminescent switching — electroluminochromism (ELC) — is one of the most powerful and promising approaches to implement controllable emission due to its facile and precise operation. Recent years have witnessed significant advances in ELC research in the context of materials development and device optimizations. This feature article reviews the fundamentals and recent progress in this emerging field, focusing on working mechanisms, materials, devices and performance improvements. Perspectives for future ELCs are also outlined.

Electroluminochromic Materials and Devices

A fluorescent naphthalimide-tetrazine dyad (NITZ) was examined for electrofluorochromism. The reversible electrochemistry of the tetrazine was accompanied by the fluorescence change through a quasi-complete energy transfer in an electrochemical cell prepared by the mixture of polymer electrolyte and naphthalimide-tetrazine dyad. Owing to the energy transfer within the dyad (naphthalimide and tetrazine), the fluorescence efficiency of NITZ was much enhanced and the effective fluorophore concentration in this system was much less than other tetrazine based electrofluorochromic device (EFD). Thus the yellow fluorescence of NITZ was switched on and off remarkably even with small quantity of NITZ (1 wt.%) in an EFD upon application of step potentials for different redox state. Furthermore, multi-color fluorescence switching was achieved by blending a naphthalimide to the electrofluorochromic layer, to show white-blue-dark state of fluorescence. Since the tetrazine and naphthalimide units have their emission quenched at different potentials, the emission color could be tuned by quenching emission at selected wavelengths, reversibly, under low working potentials.

White Electrofluorescence Switching from Electrochemically Convertible Yellow Fluorescent Dyad

Spectroelectrochemical Sensing: Current Trends and Challenges

A very sensitive technique where an electrochemical cell is coupled to a total internal reflection fluorescence microscopy setup is described and applied for the first time to the electrochemical monitoring of the fluorescence of organic dyes in solution. It is shown that this setup basically allows both spatial and time resolution for the recorded fluorescence signal as a function of the electrode potential: indeed the variations of the emission intensity are recorded within the diffusion layer for a classical cyclic voltammetry or chronoamperometry experiment inducing the redox conversion of an emissive form into a non emissive one (and conversely). Simultaneously, the variations of the emissive state lifetime are measured to discriminate between a mechanism involving only the conversion into a non emissive form from one involving a quenching between the emitter and the electrogenerated species. The results concerning the investigation of the electrochemical monitoring of the fluorescence properties for...

Electrochemical monitoring of the fluorescence emission of tetrazine and bodipy dyes using total internal reflection fluorescence microscopy coupled to electrochemistry.

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Electrochemical monitoring of the fluorescence emission of tetrazine and bodipy dyes using total internal reflection fluorescence microscopy coupled to electrochemistry.