The new fluorescent chromophore BOPHY can be readily synthesized in two steps from commercially available reagents via the coupling of pyrrole-2-carboxaldehyde with hydrazine followed by reaction with BF3. The resultant symmetric and dimeric tetracycle is composed of two BF2 units in six-membered chelate rings appended with pyrrole units on the periphery. The quantum yields of fluorescence for the unmodified compound and the tetramethyl variant are near unity, with values of 95 and 92%, respectively, in CH2Cl2. We have probed the electronic structure of this compound via cyclic voltammetry and density functional theory analysis.
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Pathway-dependent supramolecular polymerization by planarity breaking.
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