Functionalization of boron-doped tri(9,10-anthrylene)s

Hoffend, Claas; Schickedanz, Kai; Bolte, Michael; Lerner, Hans‐Wolfram

doi:10.1016/j.tet.2013.06.036

Cited by 19 publications

(10 citation statements)

References 39 publications

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“…The parent compound (R=R′=H) can readily be derivatized through hydroboration reactions to furnish brightly luminescent, yet air‐ and moisture‐sensitive products . 9,10‐Dimesityl‐9,10‐dihydro‐9,10‐diboraanthracene ( DBA ; Figure ) is long‐term stable, even under ambient conditions; a similarly stabilizing effect can be achieved through the introduction of 9‐anthryl substituents at the boron centers or by applying the concept of structural constraint . As a downside of these approaches, functionalization is now largely restricted to variations of the phenylene substituents R′.…”

Section: Introductionmentioning

confidence: 99%

“…The parent compound (R = R' = H) can readily be derivatizedthrough hydroboration reactions to furnish brightly luminescent, yet air-and moisturesensitiveproducts. [13][14][15] 9,10-Dimesityl-9,10-dihydro-9,10- [a] S. Kirschner diboraanthracene (DBA;F igure 1) is long-term stable, even under ambient conditions; [16] as imilarly stabilizing effect can be achievedt hrough the introduction of 9-anthryls ubstituents at the boronc enters [17][18][19] or by applying the concept of structural constraint. [20,21] As ad ownside of these approaches, functionalization is now largely restricted to variations of the phenylene substituents R'.Anewb ottom-up synthesis of halogenated DBAs (R' = F, Cl,Br) [22,23] was therefore required and subsequent coupling protocols had to be developed to introduce, for example, 2-thienyl moieties as R' groups.…”

Section: Introductionmentioning

confidence: 99%

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

Kirschner

Mewes

Bolte

et al. 2017

Chemistry A European J

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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 E1/2 =-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.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Kirschner

Mewes

Bolte

et al. 2017

Chemistry A European J

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“…[27][28][29][30][31][32] They have also been employed in materials chemistry for the construction of n-type semiconductors 33,34 and light-emitting polymers [35][36][37][38] that exhibit photoluminescence. [34][35][36][37][38][39][40][41][42][43][44] Heteronuclear analogues of DBA, namely, dibenzosilaborins, dibenzoazaborins, dibenzophosphaborins and dibenzochalcogenaborins (oxa, thia, selena), were also extensively studied for their applications in analytical chemistry (uoride and cyanide ion sensors) and as strong light emitters. [45][46][47][48][49][50] In addition, Jäkle and co-workers developed a synthesis for diboradiferrocene derivatives and revealed their crystal structures.…”

Section: Introductionmentioning

confidence: 99%

Efficient 8-oxyquinolinato emitters based on a 9,10-dihydro-9,10-diboraanthracene scaffold for applications in optoelectronic devices

et al. 2015

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A detailed experimental characterization and theoretical evaluation of optical as well as other relevant physicochemical properties of a series of 9,10-dihydro-9,10-diboraanthracene bis(8-oxyquinolinates) and a few other related systems is reported. The obtained compounds exhibit green luminescence with quantum yields of emission up to 63% in CH 2 Cl 2 . Single crystal X-ray diffraction studies indicate that 9,10-dihydro-9,10-diboraanthracene complexes exist either as bent conformers (stabilized by a weak intramolecular CH…O interaction bringing two 8-oxyquinolinato ligands closer to each other) or symmetrical ones (bearing both ligands related by the centre of symmetry and separated one from the other). Theoretical calculations revealed that the LUMO levels are lower for the bent conformers than for the symmetrical ones. This suggests that the luminescent properties of the studied compounds are affected by their specific structural properties. The obtained compounds were used as emitters for the construction of organic light emitting diodes (OLEDs). The highest luminance of ca. 2,000 cd·m −2 was recorded for the device containing only 2.0 wt% of 1,6-difluoro-9,10-dihydro-9,10-diboraanthracene core in the poly(Nvinylcarbazole/2-t-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PVK:PBD) matrix. The fabricated OLEDs exhibit current efficiency in the range from 0.5 to 1.1 cd·A −1 .

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“…First evidence for the successful derivatisation of 1 was gathered through its room-temperature bromination with N-bromosuccinimide in CHCl 3 . 19,21 Even though the reaction is not selective, HPLC workup finally provided an identifiable product. According to mass spectrometry, we obtained monobrominated 1 (m/z = 416); NMR spectroscopy indicated an H/Br exchange at the former phenyl ring and meta to the B atom.…”

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confidence: 99%