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000606717 1001_ $$0P:(DE-HGF)0$$aScholz, Alexander S.$$b0
000606717 245__ $$aTetramerization of BEB-Doped Phenalenyls to Obtain (BE)$_8$-[16]Annulenes (E = N, O)
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000606717 520__ $$aTwo (BE)8-[16] annulenes were prepared and fully characterized by experimental and quantum-chemical means (1,E =N;2, E=O). The 1,8-naphthalenediyl-bridged diborane(6)3 served as their common starting material, which was treated with [Al(NH$_3$)$_6$]Cl$_3$ to form 1 (91%yield) or with 1,8-naphthalenediboronic acid anhydride to form 2 (93%yield). As a result, the heteroannulenes 1 and 2 are supported by four aromatic “clamps” and may also be viewed as NH-or O-bridged cyclic tetramers of BNB-or BOB-doped phenalenyls. X-ray crystallography on mono-, di-, and tetra adducts 2*thf, 2*py$_2$, and 2*py$_4$ showed that 2 is an oligotopic Lewis acid (thf/py: tetrahydrofuran/pyridine donor). The applicability of 2 also as a Lewis basic ligand in coordination chemistry was demonstrated by the synthesis of the mononuclear Ag$^+$ complex [Ag(py)$_2$(2*py$_4$)]$^+$ and the dinuclear Pb$^{2+}$ complex 6. During the assembly of 6, the rearrangement of 2 led to the formation of two (BO)$_9$-macrocycles linked by two BOB-phenalenyls to form a nanom$eter-sized cage with four negatively charged, tetracoordinated B atoms. Both 1 and 2 show several redox waves in the cathodic regions of the cyclicvoltammograms. An in depth assessment of the consequences of electron injection on the aromaticity of 1 and 2was achieved by electronic structure calculations. 1 and 2 are proposed to exhibit aromatic switching capabilities in the [16]annulene motif.
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000606717 7001_ $$0P:(DE-HGF)0$$aBolte, Michael$$b1
000606717 7001_ $$0P:(DE-H253)PIP1026845$$aVirovets, Alexandr$$b2
000606717 7001_ $$0P:(DE-H253)PIP1027099$$aPeresypkina, Eugenia$$b3
000606717 7001_ $$00000-0003-1803-7947$$aLerner, Hans-Wolfram$$b4
000606717 7001_ $$00000-0002-3412-2511$$aAnstöter, Cate S.$$b5$$eCorresponding author
000606717 7001_ $$0P:(DE-H253)PIP1102807$$aWagner, Matthias$$b6$$eCorresponding author
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000606717 999C5 $$2Crossref$$uPyridine might serve as a ligand for the aluminum reagent and favorably influence its reactivity (e.g. by promoting the release of NH3). Moreover, it could improve the solubility of the aluminum-containing by-products in THF and thus facilitate their separation from the sparingly soluble 1.
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000606717 999C5 $$2Crossref$$uOur current working hypothesis is that 3 equiv of the starting compound 2 are consumed in the formation of one dinuclear complex 6. Although we could not prove it experimentally, it is plausible to assume that the unused fragments of the third equiv of 2 have taken up the acetate ions of Pb(OAc)2, resulting in 2 equiv of the doubly O-acetylated compound 4.
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000606717 999C5 $$2Crossref$$uThe C12B8N4-ring consists of 4 × (C1/C8a/C8) + (all B atoms) + (the 4 N atoms holding the BNB-phenalenyl subunits together).