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Regioselective Hydrogenation of a 60-Carbon Nanographene Molecule toward a Circumbiphenyl Core.

ABSTRACT: Regioselective peripheral hydrogenation of a nanographene molecule with 60 contiguous sp2 carbons provides unprecedented access to peralkylated circumbiphenyl (1). Conversion to the circumbiphenyl core structure was unambiguously validated by MALDI-TOF mass spectrometry, NMR, FT-IR, and Raman spectroscopy. UV-vis absorption spectra and DFT calculations demonstrated the significant change of the optoelectronic properties upon peripheral hydrogenation. Stimulated emission from 1, observed via ultrafast transient absorption measurements, indicates potential as an optical gain material.

SUBMITTER: Yao X 

PROVIDER: S-EPMC6728095 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Regioselective Hydrogenation of a 60-Carbon Nanographene Molecule toward a Circumbiphenyl Core.

Yao Xuelin X   Wang Xiao-Ye XY   Simpson Christopher C   Paternò Giuseppe M GM   Guizzardi Michele M   Wagner Manfred M   Cerullo Giulio G   Scotognella Francesco F   Watson Mark D MD   Narita Akimitsu A   Müllen Klaus K  

Journal of the American Chemical Society 20190226 10

Regioselective peripheral hydrogenation of a nanographene molecule with 60 contiguous sp<sup>2</sup> carbons provides unprecedented access to peralkylated circumbiphenyl (1). Conversion to the circumbiphenyl core structure was unambiguously validated by MALDI-TOF mass spectrometry, NMR, FT-IR, and Raman spectroscopy. UV-vis absorption spectra and DFT calculations demonstrated the significant change of the optoelectronic properties upon peripheral hydrogenation. Stimulated emission from 1, observ  ...[more]