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Theoretical predictions of red and near-infrared strongly emitting X-annulated rylenes
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Image of FIG. 1.
FIG. 1.

Molecular structures of (a) rylenes and (b) heteroatom X-annulated quaterrylene: X 1 = X 2 = N, N, N, N-annulated quaterrylene (QNN); X 1 = S, X 2 = N, N, S-annulated quaterrylene (QNS); X 1 = X 3 = N, NQN; X 1 = N, X 3 = S, NQS.

Image of FIG. 2.
FIG. 2.

The atomic orbital composition of selected molecular orbitals in perylene, terrylene, and quaterrylene at the B3LYP/6–31G*level.

Image of FIG. 3.
FIG. 3.

B3LYP/6–31g* HOMO (left) and LUMO (right) orbitals.

Image of FIG. 4.
FIG. 4.

The low-lying excited states of quaterrylene and the X-annulated quaterrylene calculated by using the MRCI/ZINDO. The transition oscillator strengths are given in parenthesis, and the point groups are shown for the molecules at the ground state at the bottom.

Image of FIG. 5.
FIG. 5.

(a) The absorption spectra at T = 20 K of perylene (solid for the calculated spectrum and dash dot for the experimental one); (b) the emission spectra of perylene (solid line for the T = 20 K, dash dot for T = 300 K) and their assignments of transition (vertical lines) which are labeled as N ν (N is the index of the excited normal modes and ν is the quantum number).

Image of FIG. 6.
FIG. 6.

The dominant normal modes involved in the emission spectra for perylene. The corresponding frequencies of normal modes are shown in parentheses.

Image of FIG. 7.
FIG. 7.

Theoretical emission spectra for the X-annulated quaterrylene derivatives at T = 300 K.

Image of FIG. 8.
FIG. 8.

Theoretical emission spectra for tri-N-annulated hexarylene (HNNN) and tetra-N-annulated octerylene.


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Table I.

Vertical excitation energies (eV) of the four low-lying excited states at the ground state geometry for the oligorylenes. The oscillator strengths of the dipole-allowed states are given in the parenthesis.

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Table II.

The main configurations in CASSCF wave function of the two low-lying states of oligorylenes. The orbital symmetry, and the selected weight (>0.10) in the wave function are given.

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Table III.

The frequencies of active modes involved in the emission process for the X-annulated quaterrylene derivatives.

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Table IV.

The calculated radiative and nonradiative transition rates from S1 to S0 rates for the oligorylenes and the X-annulated rylene derivatives.


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752b84549af89a08dbdd7fdb8b9568b5 journal.articlezxybnytfddd
Scitation: Theoretical predictions of red and near-infrared strongly emitting X-annulated rylenes