Synthesis, photophysical and solvatochromic properties of diacetoxyboron complexes with curcumin derivatives

2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation

“…These results are similar to those reported in the literature for photosensitizers and fluorescent synthetic diacetoxyboron complexes, also based on curcumin structure [20]. Steady-state fluorescence measurement is a comprehensive approach used to assess the excited state behavior of organic dyes in the presence of metallic species or solvents [20]. As can be seen in Figure 3A and Table 1, compound 7 shows maximum fluorescence emission in methanol, acetonitrile and toluene at 507, 504 and 443 nm, respectively (λ exc = 390 nm, a wavelength in which none of these solvents contribute for the absorption phenomenon).…”

“…In addition, compound 7 showed a higher extinction coefficient (log ε at λmax = 380, 390 and 395 nm for methanol, acetonitrile and toluene, respectively-Figure 2C and Table 1) in nonpolar and polar aprotic solvents (e.g., log ε = 4.57 in toluene), a spectroscopic behavior that is very suitable for photosensitizer and fluorescent dyes [12]. These results are similar to those reported in the literature for photosensitizers and fluorescent synthetic diacetoxyboron complexes, also based on curcumin structure [20]. Steady-state fluorescence measurement is a comprehensive approach used to assess the excited state behavior of organic dyes in the presence of metallic species or solvents [20].…”

“…In general, organic compounds based on curcumin are dyes whose structure allows them to be classified as donor-acceptor-donor species (D-A-D) due to the presence of electron donor groups at both ends of the conjugated π system and an electron acceptor group at their central portion [20]. The synthetic compound under study, i.e., compound 7, also shows a D-A-D structure (Figure 2A), with a large absorption band in about 380, 390 and 395 nm in methanol, acetonitrile and toluene, respectively (Figure 2B and Table 1).…”

Unveiling Halogen-Bonding Interactions between a Pyridine-Functionalized Fluoroborate Dye and Perfluorohaloarenes with Fluorescence Spectroscopy

“…It is known that a very efficient BF 2 -/BF-carrying fluorophores (similar to classical BODIPYs) hold a privileged spot due to high fluorescence quantum yields (FQYs) deriving from a rigid core in their structure. Similar rigidity, crucial for enhancing the radiative dissipation of excitation energy, is the characteristics of several close-relative families of dyes: boranils, , ketonates, , or ketoiminates. , Given the excellent photophysical properties of these dyes, we designed the new compound (denoted as D ) shown in Figure . Because the topology of the dye is crucial, during the design of D , we relied on the experience gained in some of our previous works.…”

An insight into the in vivo imaging potential of curcumin analogues as fluorescence probes

“…The short absorption wavelengths (ranging from 410 to 430 nm), inability to image in the near-infrared region, as well as poor chemical- and photo-stability (fast decomposition at pH ≥7 and severe fading upon photoillumination) have limited their further applications as a fluorescent dye in vivo imaging probes [3 , 11] . At present, curcumin-based probes with outstanding imaging properties for in vivo imaging have been successfully obtained by modifying the curcumin structure in order to improve both optical and in vivo dynamic properties [11] , [12] , [13] , [14] , [15] , [16] . These probes have been extensively used in the research of biomolecular marker, enzyme analysis, environmental monitoring, clinical examination, disease diagnosis, etc.…”