Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 8, Issue 1, Pages 178-190Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201200723
Keywords
aromatic substitution; density functional calculations; hexa-peri-hexabenzocoronene; substituent effects; two-photon absorption
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Funding
- MEXT, Japan [22750036, 23108705]
- Daiko Foundation
- Midcareer Researcher Program [2010-0029668]
- AFSOR/APARD [FA2386-09-1-4092]
- World Class University Programs of the Ministry of Education, Science, and Technology (MEST) of Korea [R32-2010-000-10217]
- Grants-in-Aid for Scientific Research [22750036] Funding Source: KAKEN
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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 S-0 -> S-1 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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