Synthesis, Structure, Properties, and Bioimaging of a Fluorescent Nitrogen-Linked Bisbenzothiadiazole

Abstract

This paper describes the synthesis, structure, photophysical properties, and bioimaging application of a novel 2,1,3-benzothiadiazole (BTD)-based rationally designed fluorophore. The capability of undergoing efficient stabilizing processes from the excited state allowed the novel BTD derivative to be used as a stable probe for bioimaging applications. No notable photobleaching effect or degradation could be observed during the experimental time period. Before the synthesis, the molecular architecture of the novel BTD derivative was evaluated by means of DFT calculations to validate the chosen design. Single-crystal X-ray analysis revealed the nearly flat characteristics of the structure in a syn conformation. The fluorophore was successfully tested as a live-cell-imaging probe and efficiently stained MCF-7 breast cancer cell lineages.

Facile access to deep red/near-infrared emissive AIEgens for efficient non-doped OLEDs

“…S24†). 21 The change of dipole moments from the ground state to the excited state can also characterize the TICT effect; we thus took TNB and BT-2NATPE as an example and calculated and compared the change of their dipole moments in the ground state and excited state. TNB showed dipole moments of 1.51 D and 1.05 D in the ground state and excited state, respectively, while BT-2NATPE exhibited dipole moments of 3.22 D and 2.69 D in the ground state and excited state, respectively.…”

Fluorescent Benzothiadiazole Derivatives as Fluorescence Imaging Dyes: A Decade of New Generation Probes

“…3D images of cultured 3T3 cells suggested the possibility of using BTD‐Dye‐4 as an agent for deep‐tissue imaging. A nitrogen‐linked bis‐benzothiadiazole ( BTD‐NH‐BTD , Figure 3), reported by us, [85] had the same behavior but with a green emission. The fluorophore could be used alongside the commercially available DAPI which indicated the minimum selectivity (Figure 5).…”

“…In principle, although these structures shown in Figure 3 [81][82][83][84][85][86][87][88] are not good candidates to be applied as bioimaging agents, the results obtained from the tests of these molecules may allow for the development of more selective BTDs which could, in turn, be applied as selective cell-imaging probes, as will be disclosed in the next sections of this article.…”

Preferential Mitochondrial Localization of a Goniothalamin Fluorescent Derivative

“…The lowest energy absorption bands are assigned to characteristic π–π* transitions typical from conjugated BTD derivatives. 24 On the basis of the data from Table 1 , we could describe the solvent effect in the first excited state using the microscopic solvent polarity parameters ( E T N ) in the solvatochromic method, 25 applying values provided by Reichardt. 26 Without considering water, the R 2 value obtained from the plot is 0.80, therefore in accordance with an efficient ICT from the first excited state.…”

“…These results indicate a clear ICT stabilizing process from the excited state. The lowest energy absorption bands are assigned to characteristic π–π* transitions typical from conjugated BTD derivatives . On the basis of the data from Table , we could describe the solvent effect in the first excited state using the microscopic solvent polarity parameters ( E T N ) in the solvatochromic method, applying values provided by Reichardt .…”