Napthalimide-based fluorescent probe for selective and sensitive sensing of formaldehyde and biological applications. (April 2021)

• Record Type: Journal Article
• Authors: Nasirian, Azam; Tikum, Anjong Florence; Fortibui, Maxine Mambo; Lee, Sohyun; Kim, Jinheung
• Is Part Of: Dyes and pigments. Volume 188(2021)
• Publication Date: 2021-04
• Subjects: Luminescent detection -- Formaldehyde sensing -- Napthalimide -- Condensation reaction -- Two-photon excitation; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2021.109156
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Formaldehyde (FA) is a colorless, flammable, foul-smelling chemical used in building materials and in the production of numerous household chemical products. To develop a fluorescent chemosensor for FA, a newly prepared probe 1 containing napthalimide as a fluorophore and hydrazine as a binding site of FA was designed and prepared. The amine group of the hydrazine reacts with FA to form an imide bond. Indeed, the absorption band of probe 1 at 438 nm shifted to 443 nm upon the addition of FA, indicating that the condensation reaction occurred. Also, the addition of FA to probe 1 induced a large enhancement of the emission band at 532 nm compared with the relatively very weak fluorescent emission of probe 1 alone. This high specificity toward FA was observed over other competing analytes such as Ca 2+, Mg 2+, acetaldehyde, benzaldehyde, salicylaldehyde, glucose, glutathione, Na2 S, NaHS, H2 O2, and tert -butylhydroperoxy radical. The typical two-photon dye present in probe 1 also afforded intense fluorescence upon excitation, even at 800 nm, demonstrating that probe 1 could be used for a two-photon fluorescent probe for FA sensing. Probe 1 had a quick response time in the sensing of FA at room temperature. In addition, breast cancer cells treated with probe 1 exhibited intense fluorescence imaging upon exposure to FA, indicating that probe 1 could be used for monitoring FA in living cells. This probe can lead to new possibilities for unique interactions with biological molecules for applications. Graphical abstract: We have developed a napthylimine-based dye as a one- and two-photon emission probe for the selective detection of formaldehyde. Image 1 Highlights: A new fluorescent probe of naphthylimide coupled with a pyridyl group is reported to detect formaldehyde in solution. This probe is used to minitor formaldehyde in banana and cells. The probe exhibits excellent selectivity and fast response for formaldehyde.