Dataset Information

Stereospecific Synthesis and Photophysical Properties of Propeller-Shaped C₉₀ H₄₈ PAH.

ABSTRACT: Herein, we have synthesized an enantiomerically pure propeller-shaped PAH, C₉₀ H₄₈ , possessing three [7]helicene and three [5]helicene subunits. This compound can be obtained in gram quantities in a straightforward manner. The photophysical and chiroptical properties were investigated using UV/Vis absorption and emission, optical rotation and circular dichroism spectroscopy, supported by DFT calculations. The nonlinear optical properties were investigated by two-photon absorption measurements using linearly and circularly polarized light. The extremely twisted structure and packing of the homochiral compound were investigated by single-crystal X-ray diffraction analysis.

SUBMITTER: Zhang F

PROVIDER: S-EPMC6972628 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Stereospecific Synthesis and Photophysical Properties of Propeller-Shaped C90 H48 PAH.

Zhang Fangyuan F Michail Evripidis E Saal Fridolin F Krause Ana-Maria AM Ravat Prince P

Chemistry (Weinheim an der Bergstrasse, Germany) 20191119 71

Herein, we have synthesized an enantiomerically pure propeller-shaped PAH, C90 H48 , possessing three [7]helicene and three [5]helicene subunits. This compound can be obtained in gram quantities in a straightforward manner. The photophysical and chiroptical properties were investigated using UV/Vis absorption and emission, optical rotation and circular dichroism spectroscopy, supported by DFT calculations. The nonlinear optical properties were investigated by two-photon abs ...[more]

PMID: 31742798

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Project description:The donor-acceptor-π-conjugated (D-π-)2A fluorescent dyes OUY-2, OUK-2 and OUJ-2 with two (diphenylamino)carbazole thiophene units as D (electron-donating group)-π (π-conjugated bridge) moiety and a pyridine, pyrazine or triazine ring as electron-withdrawing group (electron-accepting group, A) have been designed and synthesized. The photophysical and electrochemical properties of the three dyes were investigated by photoabsorption and fluorescence spectroscopy, Lippert-Mataga plots, cyclic voltammetry and density functional theory calculations. The photoabsorption maximum (λmax,abs) and the fluorescence maximum (λmax,fl) for the intramolecular charge-transfer characteristic band of the (D-π-)2A fluorescent dyes show bathochromic shifts in the order of OUY-2 < OUK-2 < OUJ-2. Moreover, the photoabsorption bands of the (D-π-)2A fluorescent dyes are nearly independent of solvent polarity, while the fluorescence bands showed bathochromic shifts with increasing solvent polarity (i.e., positive fluorescence solvatochromism). The Lippert-Mataga plots for OUY-2, OUK-2 and OUJ-2 indicate that the Δμ (= μe - μg) value, which is the difference in the dipole moment of the dye between the excited (μe) and the ground (μg) states, increases in the order of OUY-2 < OUK-2 < OUJ-2. Therefore, the fact explains our findings that OUJ-2 shows large bathochromic shifts of the fluorescence maxima in polar solvents, as well as the Stokes shift values of OUJ-2 in polar solvents are much larger than those in nonpolar solvents. The cyclic voltammetry of OUY-2, OUK-2 and OUJ-2 demonstrated that there is little difference in the HOMO energy level among the three dyes, but the LUMO energy levels decrease in the order of OUY-2 > OUK-2 > OUJ-2. Consequently, this work reveals that for the (D-π-)2A fluorescent dyes OUY-2, OUK-2 and OUJ-2 the bathochromic shifts of λmax,abs and λmax,fl and the lowering of the LUMO energy level are dependent on the electron-withdrawing ability of the azine ring, which increases in the order of OUY-2 < OUK-2 < OUJ-2.

Dataset Information

Stereospecific Synthesis and Photophysical Properties of Propeller-Shaped C₉₀ H₄₈ PAH.

Publications

Stereospecific Synthesis and Photophysical Properties of Propeller-Shaped C<sub>90</sub> H<sub>48</sub> PAH.

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