New Red-Shifted 4-Styrylcoumarin Derivatives as Potential Fluorescent Labels for Biomolecules

Abstract

Important scientific areas, such as cellular biology, medicine, pharmacy, and environmental sciences, are dependent on very sensitive analytical techniques to track and detect biomolecules. In this work, we develop a simple, low-cost and effective synthetic strategy to produce new red-shifted 4-styrylcoumarin derivatives as promising inexpensive fluorescent labels for biomolecules. The extension of the delocalized π-electron system results in bathochromic shifts in these new coumarin derivatives, which also present large Stokes shifts. In addition, density functional theory and time-dependent density functional theory calculations helped to rationalize the photophysical properties observed by the experimental results.

Self-assembled superstructures derived from suitably substituted phenanthro[9,10-d] imidazole-based Zn(ii)/Cd(ii) complexes for selective detection of acetone

“…Conversely, L3 metal complexes show a substantial bathochromic shift compared to L1 metal complexes (B59-66 nm) due to the combined effects of solvent polarity enhanced ICT transitions. [67][68][69] The calculated quantum yields of these metal complexes at their respective ICT based emission maxima are tabulated in Table 1. Therefore, the difference in the electron donating and withdrawing ability of the functionalized terminal phenyl ring can significantly influence the energy differences between the frontier molecular orbitals (FMOs) and is responsible for the disparity in optical responses.…”

Synthesis and Characterisation of Fluorescent Novel Pt(II) Cyclometallated Complexes with Anticancer Activity

“…Fluorescence is increasingly becoming a point of interest in medicinal chemistry, with molecules' photodynamic properties being used for targeting, tracking, photoactivation, theragnostics, and ROS generation [30,[33][34][35]. The fluorescence excitation and emission maxima (Em max and Ex max ) were determined for each complex (Table 2).…”

Rational Design of Cost-Effective 4-Styrylcoumarin Fluorescent Derivatives for Biomolecule Labeling

“…Synthesis of 6-(4-formylphenoxy)hexanoic acid derivative (4) was performed according to the method described by Eustáquio et al [27].…”

“…Additionally, it is widely recognized that the inclusion of such substituents, forming donor-π-bridge-acceptor (D-π-A) structures, can facilitate an efficient intramolecular charge transfer (ICT) process. This, in turn, leads to remarkable and varied photophysical properties in coumarin derivatives [10,[27][28][29][30][31][32][33][34]. Several of these coumarin derivatives have been applied in many important areas such as solar cells, organic light-emitting diodes, and fluorescent probes [26,[35][36][37].…”