Combined experimental and theoretical study of one- and two-photon absorption properties of D–π–A–π–D type bis(carbazolylfluorenylethynyl) arene derivatives: Influence of aromatic acceptor bridge

Devi, Chebrolu Lavanya; Yesudas, Kada; Makarov, Nikolay S.; Rao, V. Jayathirtha; Bhanuprakash, K.; Perry, Joseph W.

doi:10.1016/j.dyepig.2014.09.027

Cited by 31 publications

(9 citation statements)

References 67 publications

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“…The D-A-D motif of our substituted compounds suggests they are quadrupolar-type molecules. These are favorable as TPA materials because of their intrinsic intramolecular charge transfer from the periphery donors to the central acceptor upon excitation . The symmetrical charge distribution between the center and the ends of the molecule have been highly correlated to large two-photon cross sections .…”

Section: Resultsmentioning

confidence: 99%

“…These are favorable as TPA materials because of their intrinsic intramolecular charge transfer from the periphery donors to the central acceptor upon excitation. 82 The symmetrical charge distribution between the center and the ends of the molecule have been highly correlated to large two-photon cross sections. 83 Altering the acceptor strength from nitrogen to sulfur to selenium can modulate the excited-state properties of the molecules and affect γ, therefore affecting TPA cross section of the compound.…”

Section: Methodsmentioning

confidence: 99%

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Investigations of Thienoacene Molecules for Classical and Entangled Two-Photon Absorption

et al. 2018

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Investigations of the optical effects in thienoacene chromophores with different central atoms were performed. These chromophores provide a basis for the comparison of the linear, two-photon, and entangled two-photon properties in organic molecules with varying degrees of dipolar or quadrupolar character. Linear absorption and emission as well as time-dependent density functional theory calculations were performed for the chromophores investigated. Measurements of the classical two-photon absorption (TPA), entangled two-photon absorption (ETPA), as well as entangled two-photon fluorescence were experimentally performed for the four chromophores. Electronic structure calculations were utilized to provide estimates of the classical two-photon absorption coefficients. The results of the measured entangled two-photon cross sections were compared with theoretical estimates for the molecules investigated. It is found that the dipole (transition or permanent) pathway can have an effect on the trends in the entangled photon absorption process in dipolar organic chromophores. This study helps predict the properties of the entangled twophoton effect in chromophores with different dipolar and quadrupolar character.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Investigations of Thienoacene Molecules for Classical and Entangled Two-Photon Absorption

et al. 2018

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“…Finally, when eq is introduced in eq , the TPA cross-section in macroscopic units becomes Here, N is 4, and the broadening factor, Γ, is taken as 0.10 eV (Γ = 3.6749326 × 10 –3 in au). ,, The unit of the TPA cross-section is GM, and 1 GM corresponds to 10 –50 cm 4 s photon –1 .…”

Section: Methodsmentioning

confidence: 99%

“…Here, N is 4, and the broadening factor, Γ, is taken as 0.10 eV (Γ = 3.6749326 × 10 −3 in au). 26,32,54 The unit of the TPA…”

Section: ■ Computational Methodsmentioning

confidence: 99%

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Two-Photon Absorption Properties of Gold Fluorescent Protein: A Combined Molecular Dynamics and Quantum Chemistry Study

Şımşek

Brown

2018

J. Phys. Chem. B

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Molecular dynamics (MD) simulations were carried out to obtain the conformational changes of the chromophore in the gold fluorescent protein (PDB ID: 1OXF ). To obtain two-photon absorption (TPA) cross-sections, time dependent density functional theory (TD-DFT) computations were performed for chromophore geometries sampled along the trajectory. The TD-DFT computations used the CAM-B3LYP functional and 6-31+G(d) basis set. Results showed that two dihedral angles change remarkably over the simulation time. TPA cross-sections were found to average 13.82 GM for the excitation to S computed from the equilibrium geometries; however, extending the structures with a water molecule and GLU residue, which make H bonds with the chromophore molecule, increased excitation energies and TPA cross-sections significantly. Besides the effects of the surrounding residues and the dihedrals on the spectroscopic properties, some bond lengths affected the excitation energies and the TPA cross-sections significantly (up to ±25-30%), while the effects of the bond angles were smaller (±5%). Overall the present results provide insight into the effects of the conformational flexibility on TPA (with gold fluorescent protein as a specific example) and suggest that further experimental measurements of TPA for the gold fluorescent protein should be undertaken.

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Palladium‐Catalyzed Domino Process to Construct 2,3,9,9a‐Tetrahydro‐1H‐Fluorene Derivatives:Transient σ‐Alkylpalladium(II) Complex Mediated C(sp²)‐H Bond Activation

et al. 2019

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A palladium‐catalyzed cascade reaction involving domino Heck/intramolecular C−H arylation to construct 2,3,9,9a‐tetrahydro‐1H‐fluorene derivatives was developed. Products are obtained in moderate to excellent yields. The transient σ‐alkylpalladium(II) complex is the key intermediate, which mediates the C(sp2)‐H bond activation via a six‐metallacycle. According to a transient σ‐alkylpalladium(II) complex, the control experiment demonstrates that β‐H elimination is faster than C−H activation. The methodology shows high chemoselectivity and good functional group tolerance.

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Combined experimental and theoretical study of one- and two-photon absorption properties of D–π–A–π–D type bis(carbazolylfluorenylethynyl) arene derivatives: Influence of aromatic acceptor bridge

Cited by 31 publications

References 67 publications

Investigations of Thienoacene Molecules for Classical and Entangled Two-Photon Absorption

Investigations of Thienoacene Molecules for Classical and Entangled Two-Photon Absorption

Two-Photon Absorption Properties of Gold Fluorescent Protein: A Combined Molecular Dynamics and Quantum Chemistry Study

Palladium‐Catalyzed Domino Process to Construct 2,3,9,9a‐Tetrahydro‐1H‐Fluorene Derivatives:Transient σ‐Alkylpalladium(II) Complex Mediated C(sp²)‐H Bond Activation

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Combined experimental and theoretical study of one- and two-photon absorption properties of D–π–A–π–D type bis(carbazolylfluorenylethynyl) arene derivatives: Influence of aromatic acceptor bridge

Cited by 31 publications

References 67 publications

Investigations of Thienoacene Molecules for Classical and Entangled Two-Photon Absorption

Investigations of Thienoacene Molecules for Classical and Entangled Two-Photon Absorption

Two-Photon Absorption Properties of Gold Fluorescent Protein: A Combined Molecular Dynamics and Quantum Chemistry Study

Palladium‐Catalyzed Domino Process to Construct 2,3,9,9a‐Tetrahydro‐1H‐Fluorene Derivatives:Transient σ‐Alkylpalladium(II) Complex Mediated C(sp2)‐H Bond Activation

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Palladium‐Catalyzed Domino Process to Construct 2,3,9,9a‐Tetrahydro‐1H‐Fluorene Derivatives:Transient σ‐Alkylpalladium(II) Complex Mediated C(sp²)‐H Bond Activation