Synthesis, fluorescence-sensing and molecular logic of two water-soluble 1,8-naphthalimides

A Highly Water-Soluble and Solid State Emissive 1,8-Naphthalimide as a Fluorescent PET Probe for Determination of pHs, Acid/Base Vapors, and Water Content in Organic Solvents

“…Herein we are reporting on a highly water-soluble probe based on 1,8-naphthalimide fluorophore (Scheme 1). This work is an extension of our previous report, where two amidoamine containing 1,8-naphthalimides with water solubility in a concentration of 10 −5 mol/L was described [38]. In contrast, the novel compound showed higher water solubility resulting in stable water solutions even at concentrations 10 −2 mol/L.…”

“…This encouraged us to investigate the photophysical behavior of the probe in a pure water solution. Due to the ICT nature of the 1,8-naphthalimide unit, compound 4 showed absorption long-wavelength band from 290 nm to 380 nm with maximal intensity at 344 nm (Figure 1) and fluorescence signaling output in the range between 350 nm and 480 nm with a maximum at 397 nm (Figure 2) [38,53]. The observed absorption spectra were pH-independent, which is illustrated in Figure 1, where the absorption spectra of probe 4 at pH 3, pH 7, and pH 11 are depicted as an example.…”

Fluorescent‐Labeled Octasilsesquioxane Nanohybrids as Potential Materials for Latent Fingerprinting Detection

“…Again, both ANP and PANP possessed emission bands that were found to be highly red shifted (≈54 nm and ≈54 nm, respectively) from the non‐interacting solvent hexane to polar DMF and a decrease of the fluorescence quantum yield was obtained for PANP especially in non‐polar solvents; this fact could be attributed to the better solubility of PANP that would facilitate the formation of complexes in the ground state or internal transfer processes. In this context, choice of PANP instead of PANA gave rise to a “OFF‐ON” irreversible switch system possessing “receptor‐fluorophore‐receptor” architectural model (Figure S13) . Furthermore, computational calculations based on TDDFT//B3LYP/6‐31G(d) level of theory supported the use of the piperazine moiety (Table ).…”

“…In this context, choice of PANP insteado fPANA gave rise to a" OFF-ON" irreversible switch system possessing "receptor-fluorophore-receptor" architectural model ( Figure S13). [41] Furthermore, computational calculations based on TDDFT//B3LYP/6-31G(d) level of theory [42] supported the use of the piperazine moiety (Table 1). Hence, the heavy atom Br presenta tt he naphthalimide fluorophorei nPANA inducedanon-radiative transition with oscillator strength (f)o f0 .0028 justifying its dark state forbidden S 0 !S 1 transitionw hich was non-fluorescent.…”

Synthesis and Fluorescent Property Study of Novel 1,8-Naphthalimide-Based Chemosensors

“…In this study, we designed and synthesized a series of N -n-butyl-1,8-naphthalimide fluorescent sensors with a diethyl amino link at the C -4 position. As shown in Scheme 1 , a functional group containing a nitrogen atom and a carbonyl group was introduced to 1,8-naphthalimide; these groups are commonly used as acceptor units in probes designed for metal ions and anions [ 22 , 23 ]. The biological importance of the combination of the carbonyl groups with naphthalimide prompted us to explore a new class of fluorescent probe for selective recognition of metal ions in aqueous media.…”