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Keywords:

  • boracycles;
  • conjugation;
  • electrochemistry;
  • photochemistry;
  • pi interactions

Abstract

A series of diarene-fused 1,2-dihydro-1,2-diborins were prepared as a new B[BOND]B-bond-embedded polycyclic π-electron system. The reduction of these compounds with metals produced their corresponding dianions, the π-conjugation modes of which varied from 6π-conjugation within the central 1,2-diborin skeleton to 14π peripheral conjugation over the tricyclic skeleton, depending on the nature of the reduced biaryl framework. Moreover, the countercation to the dianions had a significant effect on the absorption spectra, with a dramatic color change from yellow to deep blue, depending on the distance between the tricyclic dianion skeleton and the countercation.

Featured Compounds

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  1. 1 - 11
Compound 1
Molecular Weight:274.021
Molecular Formula:C12H16B2N2S2
InChIKey:VBWIUZDELPOVRT-UHFFFAOYSA-N
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Compound 12−
Molecular Weight:274.021
Molecular Formula:C12H16B2N2S2
InChIKey:CZADQTXHNACQFG-UHFFFAOYSA-N
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Compound 42−
Molecular Weight:161.848
Molecular Formula:C8H16B2N2
InChIKey:FVOQODBMPIGWGM-UHFFFAOYSA-N
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Compound 5
Molecular Weight:269.581
Molecular Formula:C4H12B2Br2N2
InChIKey:AAIAPDRRFGTGCQ-UHFFFAOYSA-N
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Compound 22−
Molecular Weight:274.021
Molecular Formula:C12H16B2N2S2
InChIKey:KICHNLLADDXKTA-UHFFFAOYSA-N
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Compound 32−
Molecular Weight:261.965
Molecular Formula:C16H20B2N2
InChIKey:IQWRYGLLKILFNT-UHFFFAOYSA-N
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Compound 2
Molecular Weight:274.021
Molecular Formula:C12H16B2N2S2
InChIKey:KWOXHLJAIYOSGT-UHFFFAOYSA-N
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Compound 22−·2[K+([2.2.2]cryptand)]
Molecular Weight:1105.194
Molecular Formula:C48H88B2K2N6O12S2
InChIKey:VFDKLYDWIIVUTG-UHFFFAOYSA-N
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Compound 22−·2K+
Molecular Weight:352.217
Molecular Formula:C12H16B2K2N2S2
InChIKey:FWGQRHXSTQDFEK-UHFFFAOYSA-N
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Compound 22−·2[Li+(OMe2)2]
Molecular Weight:472.177
Molecular Formula:C20H40B2Li2N2O4S2
InChIKey:JVVDCSJXKMYCPN-UHFFFAOYSA-N
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Compound 22−·2[K+(OMe2)3]
Molecular Weight:628.628
Molecular Formula:C24H52B2K2N2O6S2
InChIKey:KGYTWNSHTRKFPB-UHFFFAOYSA-N
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  1. 1 - 11