Abstract
Nitro-substituted π-electronic molecules are fascinating because of their unique electronic and optical properties and the ease of their transformation into various functional derivatives. Herein, nitro-introduced dipyrrolyldiketone BF2 complexes as anion-responsive π-electronic molecules were synthesized, and their electronic properties and anion-binding abilities were investigated by spectroscopic analyses and theoretical studies. The obtained nitro-substituted derivatives showed solvent-dependent UV/vis spectral changes and high anion-binding affinities due to the easily pyrrole-inverted conformations and polarized pyrrole NH sites upon the introduction of electron-withdrawing moieties.
Highlights
Designed π-electronic systems have unique electronic and optical properties and assembling behavior [1,2,3,4,5,6,7]
Pyrrole inversions of dipyrrolyldiketone BF2 complexes, whose pyrrole NH sites are oriented to the side of the carbonyl units, are required for anion binding [15,16,17,18,19]
Optimized structures were calculated at the B3LYP level by using the 6-31G(d,p) basis set for C, H, B, N, O, and F and the LanL2DZ basis set for I, and time-dependent denfunctional theory (TD-DFT)-based theoretical spectra were calculated at CPCM-B3LYP/6-31+G(d,p) (CH2 Cl2 )//B3LYP/6-31G(d,p)
Summary
Designed π-electronic systems have unique electronic and optical properties and assembling behavior [1,2,3,4,5,6,7]. The properties of π-electronic systems can be modulated by the substituents and resulting structures. NO2 -substituted molecules are converted to the corresponding amines, which are the precursors of amides and other derivatives with functional groups. It is noteworthy that nitroarenes behave as electrophilic coupling partners for Suzuki–. The anion-binding properties depend on the substituents, such as ethyl and fluorine groups, introduced onto the pyrrole rings [16,17]. Compared to 1a, 1b shows less affinities for anions due to the electron-donating β-ethyl substituents. The introduction of nitro group(s) at the pyrrole α-positions was investigated for modulating the electronic states and anion-binding abilities.
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