A simple BODIPY-aniline-based fluorescent chemosensor as multiple logic operations for the detection of pH and CO₂gas

Abstract

A simple 4-aniline boron-dipyrromethene (BODIPY) dye (1) was developed as a highly sensitive acidic pH fluorescent probe excitable with visible light based on a photoinduced electron transfer (PeT) mechanism. The pH titration indicates that the fluorescence intensity increases more than 500-fold within the pH range of 4.12-1.42 with a pKa value of 3.24 in methanol-water (1 : 1, v/v) solution, which is valuable for studying strongly acidic conditions. Density functional theory (DFT) calculations reproduce the fluorescence off-on behavior. 1 has also been used as a fluorescent chemosensor for the visual detection of dissolved carbon dioxide (CO2) gas. The underlying mechanism of the sensing process is rationalized. This probe can be recovered by bubbling nitrogen (N2) gas into CO2-treated solutions for over 10 cycles. In addition, two logic gates (OR and INH) have been achieved at the molecular level by changing the initial states of system 1 and chemical inputs.

Theoretical study of the photophysical processes of a styryl‐bodipy derivative eliciting an AND molecular logic gate response

“…However, a significant rise of information processing molecular devices is expected in the forthcoming years . Theoretical studies aiming to provide experimentalists with information regarding a potential MLG candidate or to gain insight into experimental findings can play a significant role in the field of MLG …”

When Push Comes to Shove: Unravelling the Mechanism and Scope of Nonemissive meso-Unsaturated BODIPY Dyes

“…Calculated energy diagrams of 1 (top panel) and 2 (bottom panel)22 at the B3LYP/6-31g(d) level with an applied polarizable continuum model solvation of acetonitrile. Ground state (left) and excited state (right) optimized geometries are shown.…”

A New Rhodamine B‐based Fluorescent Probe for pH Detection and Bioimaging under Strong Acidic Conditions

“…The metal salts used were Al(NO 3 1 H and 13 C NMR (nuclear magnetic resonance) spectra (at 400 MHz and 100 MHz, respectively) were recorded in CDCl 3 with tetramethylsilane as internal reference on a Bruker Advance500 FT spectrometer. Deionized water was used throughout the experiment.…”

“…14,[18][19][20] Relatively less attention has been paid to fluorescent probes, which are promising candidates for pH detection in the lower pH region (pH < 4). 3 In fact, some media such as those found in the human stomach 21,22 or environmental water 3 are strongly acidic and certain microorganisms, including Helicobacter pylori and "acidophiles" favor such harsh conditions, therefore it is necessary to develop chemosensors for indicating pH levels of these highly acidic media.…”