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Keywords:

  • aromatic substitution;
  • density functional calculations;
  • hexa-peri-hexabenzocoronene;
  • substituent effects;
  • two-photon absorption

Abstract

We have demonstrated that the iridium-catalyzed direct borylation of hexa-peri-hexabenzocoronene (HBC) enables regioselective introduction of boryl groups to the para-, ortho-, and meta-substituted HBCs in high yields. The boryl groups have been transformed into various functionalities such as hydroxy, cyano, ethynyl, and amino groups. We have elucidated that the substituents significantly influence the photophysical properties of HBCs to enhance fluorescence quantum yields. DFT calculations revealed that the origin of the substituent effect is the lift in degeneracy in the frontier orbitals by an interaction with electron-donating and electron-withdrawing substituents at the para- and ortho-positions. The change in molecular orbitals results in an increase of the transition probability from the S0[RIGHTWARDS ARROW]S1 states. In addition, the two-photon absorption cross-section values of para-substituted HBCs are significantly larger than those of ortho- and meta-substituted HBCs.

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Featured Compounds

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  1. 1 - 28
Compound 1a
Molecular Weight:995.2951
Molecular Formula:C78H58
InChIKey:ZRSDGNRBUBDUSB-UHFFFAOYSA-N
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Compound 1b
Molecular Weight:995.2951
Molecular Formula:C78H58
InChIKey:AOWRHGHYYVEZKM-UHFFFAOYSA-N
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Compound 1c
Molecular Weight:877.1194
Molecular Formula:C69H48
InChIKey:KQCAOVVXRRNLTA-UHFFFAOYSA-N
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Compound 2b
Molecular Weight:1247.218
Molecular Formula:C90H80B2O4
InChIKey:NBQFVLPIQPEPDZ-UHFFFAOYSA-N
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Compound 2a
Molecular Weight:1247.218
Molecular Formula:C90H80B2O4
InChIKey:LFTWMBNVAXPSBB-UHFFFAOYSA-N
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Compound 2c
Molecular Weight:1255.003
Molecular Formula:C87H81B3O6
InChIKey:FMBWKSJBYWNDIY-UHFFFAOYSA-N
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Compound 3a
Molecular Weight:1027.294
Molecular Formula:C78H58O2
InChIKey:UIHKHHCULDDKNR-UHFFFAOYSA-N
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Compound 3c
Molecular Weight:925.1176
Molecular Formula:C69H48O3
InChIKey:WSRFPWRYVGNJMK-UHFFFAOYSA-N
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Compound 3b
Molecular Weight:1027.294
Molecular Formula:C78H58O2
InChIKey:RBRIESHSUJHUNC-UHFFFAOYSA-N
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Compound 5a
Molecular Weight:1055.347
Molecular Formula:C80H62O2
InChIKey:SLAJVAJHMSIQQW-UHFFFAOYSA-N
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Compound 4a
Molecular Weight:1291.417
Molecular Formula:C80H56F6O6S2
InChIKey:GHGMULQXMBDXRD-UHFFFAOYSA-N
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Compound 6a
Molecular Weight:1155.5507
Molecular Formula:C90H74
InChIKey:QIGJLDJFGCOFRX-UHFFFAOYSA-N
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Compound 6b
Molecular Weight:1155.5507
Molecular Formula:C90H74
InChIKey:HEFSYSOIXDHRCX-UHFFFAOYSA-N
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Compound 6c
Molecular Weight:1117.5026
Molecular Formula:C87H72
InChIKey:XRHLJXPBLZEJIS-UHFFFAOYSA-N
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Compound 7a
Molecular Weight:1261.6758
Molecular Formula:C96H80N2
InChIKey:XLKULNRIIXCXOM-UHFFFAOYSA-N
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Compound 7b
Molecular Weight:1261.6758
Molecular Formula:C96H80N2
InChIKey:RXIRWXSLMJSFQN-UHFFFAOYSA-N
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Compound 8a
Molecular Weight:1045.314
Molecular Formula:C80H56N2
InChIKey:DIPFERHIJHKJRO-UHFFFAOYSA-N
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Compound 8b
Molecular Weight:1045.314
Molecular Formula:C80H56N2
InChIKey:LXLZLLKOZZUEDW-UHFFFAOYSA-N
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Compound 8c
Molecular Weight:952.1478
Molecular Formula:C72H45N3
InChIKey:SKIQWVYFOKMAAA-UHFFFAOYSA-N
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Compound 4b
Molecular Weight:1291.417
Molecular Formula:C80H56F6O6S2
InChIKey:SEUDNNPXNLTUGT-UHFFFAOYSA-N
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Compound 5b
Molecular Weight:1055.347
Molecular Formula:C80H62O2
InChIKey:UITDKBOBFNGURS-UHFFFAOYSA-N
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Compound 4c
Molecular Weight:1321.303
Molecular Formula:C72H45F9O9S3
InChIKey:HACXBYBRJNFBSE-UHFFFAOYSA-N
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Compound I
Molecular Weight:522.5923
Molecular Formula:C42H18
InChIKey:IVJZBYVRLJZOOQ-UHFFFAOYSA-N
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Compound II-a
Molecular Weight:580.6748
Molecular Formula:C44H24N2
InChIKey:BINNTYDSKIXUCN-UHFFFAOYSA-N
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Compound II-b
Molecular Weight:580.6748
Molecular Formula:C44H24N2
InChIKey:OGCIFYQZVDQGDW-UHFFFAOYSA-N
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Compound III-a
Molecular Weight:572.6112
Molecular Formula:C44H16N2
InChIKey:BOAMGGJBMGOKLG-UHFFFAOYSA-N
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Compound III-b
Molecular Weight:572.6112
Molecular Formula:C44H16N2
InChIKey:DVGAMPPZVAVBLJ-UHFFFAOYSA-N
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Compound III-c
Molecular Weight:597.6207
Molecular Formula:C45H15N3
InChIKey:FORIYBKMQLRFHC-UHFFFAOYSA-N
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