1040432-76-5

Upstream product

• 1040432-70-9 6,13-dibromo-6,13-dihydro-6,13-diborapentacene 
• 5806-59-7 mesityllithium 
• 636-28-2 1,2,4,5-tetrabromobenzene 
• 106750-88-3 6,7-dibromo-1,4-epoxy-1,4-dihydronaphthalene 
• 2633-66-1 2-mesitylmagnesium bromide 
• 13214-70-5 2,3-dibromonaphthalene 
• 184633-78-1 2,3-bis(trimethylsilyl)naphthalene 

Relevant academic research and scientific papers

Syntheses and structures of 6,13-dihydro-6,13-diborapentacenes: π-stacking in heterocyclic analogues of pentacene

6,13-Dibromo-6,13-dihydro-6,13-diborapentacene (1) has been prepared by the reaction of 2,3-bis(trimethylsilyl)-naphthalene with BBr3. The reaction of 1 with Me4Sn or mesityllithium afforded the dimethyl derivative 2 or the dimesityl derivative 3, respectively. In the solid state compounds 1 and 2 form cofacial π-stacks along the a crystal axes, albeit in slightly different ways.

How Boron Doping Shapes the Optoelectronic Properties of Canonical and Phenylene-Containing Oligoacenes: A Combined Experimental and Theoretical Investigation

Optimized syntheses of 6,13-dimesityl-6,13-dihydro-6,13-diborapentacene (DBP) and a related compound (DBI) featuring two biphenylene-2,3-diyl units in place of naphthalene-2,3-diyl moieties are reported. Striking differences between the optoelectronic properties of DBP and DBI have been experimentally observed, and explained by quantum chemical calculations. DBP is a member of the oligoacene family, DBI is a linear [N]phenylene derivative. The yellow DBP shows blue photoluminescence, the deep red DBI is nonfluorescent. Both compounds give rise to two reversible redox transitions at E12 =?2.03 V, ?2.75 V (DBP) and ?1.52 V, ?2.30 V (DBI; THF, vs. FcH/FcH+). The higher electron affinity of DBI agrees with a lower calculated LUMO energy level [?0.57 eV for DBI with respect to DBP @HF//SCS-MP2/def2-TZVP] and a higher Lewis acidity of its boron centers, which is reflected in the trend of adduct formation with small Lewis bases (MeCN, F?). The thermochemistry underlying this trend, as well as the mechanism of fluorescence quenching in DBI, are revealed by state-of-the-art quantum chemical calculations. It is suggested that the nonradiative deactivation occurs via a low-lying, doubly excited state.