NIR optical carbon dioxide sensors based on highly photostable dihydroxy-aza-BODIPY dyes

Abstract

A new class of pH-sensitive indicator dyes for optical carbon dioxide sensors based on di-OH-aza-BODIPYs is presented. These colorimetric indicators show absorption maxima in the near infrared range (λ_max 670–700 nm for the neutral form, λ_max 725–760 nm for the mono-anionic form, λ_max 785–830 nm for the di-anionic form), high molar absorption coefficients of up to 77 000 M⁻¹ cm⁻¹ and unmatched photostability. Depending on the electron-withdrawing or electron-donating effect of the substituents the pK_a values are tunable (8.7–10.7). Therefore, optical carbon dioxide sensors based on the presented dyes cover diverse dynamic ranges (0.007–2 kPa; 0.18–20 kPa and 0.2–100 kPa), which enables different applications varying from marine science and environmental monitoring to food packaging. The sensors are outstandingly photostable in the absence and presence of carbon dioxide and can be read out via absorption or via the luminescence-based ratiometric scheme using the absorption-modulated inner-filter effect. Monitoring of the carbon dioxide production/consumption of a Hebe plant is demonstrated.