NIR-fluorescent coumarin-fused BODIPY dyes with large Stokes shifts

Abstract

A series of novel non-symmetrical coumarin-fused BODIPY dyes were synthesised. Their absorption and emission properties are strongly influenced by substitution in the coumarin moiety. Diethylamino-substituted dyes showed near-IR emission with large Stokes shifts (up to 144 nm) and good fluorescence quantum yields.

Optical signatures of borico dyes: a TD-DFT analysis

“…The vibronic spectra for a model molecule presenting the skeleton of 6 are shown in Figure 8, whereas Figure 9 gives the density difference plots obtained for 6a and 6c. On the former graph, one notices the presence of a shoulder, consistently with experiment [12], but its height is slightly underestimated, a result typical of BODIPY structures [38]. The changes compared to Figure 4 are nevertheless obvious and in the line of the measurements.…”

“…To the best of our knowledge, there is absolutely no previous theoretical investigation of these exciting structures, and this contribution aims to fill this gap. Note that, we found two other works dealing with joint coumarin-BODIPY emitters: on the one hand, the 2011 anion-sensing dimer of Cao et al in which the two chromogens are separated by a short conjugated segment [11] and, on the other hand, the very recent work of Bochkov and coworkers who synthesized four different fused coumarin-BODIPY dyes [12], that we model in the last Section of the present paper. Amongst all possible first-principle approaches for investigating excited-state properties, Time-Dependent Density Functional Theory (TD-DFT) is certainly the most popular, with a continuously increasing number of published applications [13][14][15][16].…”

“…As stated in the Introduction, new coumarin-BODIPY structures, presenting a completely different architecture, appeared two months ago [12]. These molecules are displayed in Figure 7, and Table 3 reports key data computed with exactly the same computational protocol as the one used above.…”

Novel Iminocoumarin Derivatives: Synthesis, Spectroscopic and Computational Studies

“…In recent years, synthesis and applications of fluorescent materials happen to be a fruitful research activity [1][2][3][4]. In the field of functional materials, designing and development of innovative fluorescent molecules for high-tech applications is very demanding [1][2][3][4].…”

A Selective, Colorimetric and Ratiometric Chemosensor for Hg2+ and Its Application as Test Papers

“…25 Besides, other kinds of coumarin-based sensors have also been developed based-on intra-molecular charge transfer (ICT) 26,27 or fluorescence resonance energy transfer (FRET). 28 However, much work is required to synthesize the above-mentioned sensor molecules. In Chang and coworker's work, they developed a new kind of coumarin-based sensor that can respond to Hg 2+ via a desulfurization process; this work paves a way to develop easily-prepared Hg 2+ sensors.…”