Organometallics p. 2818 - 2823 (2019)
Update date:2022-08-10
Topics:
Kirschner, Sven
Uecker, Ise
Bolte, Michael
Lerner, Hans-Wolfram
Wagner, Matthias
Linear annulation of two 2,3-biphenylenediyl moieties to a 1,4-dibora-2,5-cyclohexadiene core via its carbon atoms leads to the boron-doped phenylene-containing oligoacene (B-POA) DBI. The optoelectronic properties of DBI are unlike those of related boron-doped polycyclic aromatic hydrocarbons (B-PAHs), such as 6,13-dihydro-6,13-diborapentacene (DBP). Herein we disclose two new B-POAs, which provide insight into fundamental structure-property relationships. The first is a π-extended DBI congener (e-DBI), in which two 2,3-benzo[b]biphenylenediyl moieties are linearly annulated to the central B2C4 ring and behaves partly similar to DBI: it is a strong electron acceptor and has a deep red color. In contrast to the nonluminescent DBI, it shows red fluorescence (quantum yield: 12%), which changes to blue-green upon addition of excess F--ions. In the presence of 0.4 equiv of F-, nearly white emission is observed (CIE1931: (0.3320|0.4056)). If biphenylenediyl moieties are angularly attached to the B2C4 ring via their 1,2-positions, the resulting mixture of "v"- and "z"-shaped B-POA isomers (v/z-DBI) behaves distinctly different from linear DBI: the electrode potentials required for the reversible two-electron reductions of v/z-DBI are significantly more cathodic, and v/z-DBI is an orange rather than red solid and emits green light (quantum yields 65%) upon irradiation.
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(2019)