Quadrupolar Chromophores for Voltage Sensing and White‐Light Generation

Painelli, Anna; Terenziani, Francesca

doi:10.1002/cphc.200800648

Cited by 6 publications

(3 citation statements)

References 16 publications

(23 reference statements)

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“…Charge-transfer chromophores represent a wide class of π-conjugated molecules where the presence of electron-donor (D) and -acceptor (A) groups ensures the occurrence of low-energy excited states with large transition dipole moments. Polar (D-π-A) chromophores are good polarity sensors − and may show large nonlinear optical response, − and some of them behave as molecular rectifiers. − Quadrupolar (D-π-A-π-D or A-π-D-π-A) dyes were specifically developed as two-photon absorbers, − and some of them proved particularly interesting for two-photon-induced photodynamic therapy. − The important fluorescence solvatochromism shown by some quadrupolar dyes makes them also interesting for polarity- and voltage-sensing applications, , while quadrupolar structures were recently considered as light-harvesting species in solar cells …”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Characterization and Modeling of Quadrupolar Charge-Transfer Dyes with Bulky Substituents

et al. 2012

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Joint experimental and theoretical work is presented on two quadrupolar D-π-A-π-D chromophores characterized by the same bulky donor (D) group and two different central cores. The first chromophore, a newly synthesized species with a malononitrile-based acceptor (A) group, has a V-shaped structure that makes its absorption spectrum very broad, covering most of the visible region. The second chromophore has a squaraine-based core and therefore a linear structure, as also evinced from its absorption spectra. Both chromophores show an anomalous red shift of the absorption band upon increasing solvent polarity, a feature that is ascribed to the large, bulky structure of the molecules. For these molecules, the basic description of polar solvation in terms of a uniform reaction field fails. Indeed, a simple extension of the model to account for two independent reaction fields associated with the two molecular arms quantitatively reproduces the observed linear absorption and fluorescence as well as fluorescence anisotropy spectra, fully rationalizing their nontrivial dependence on solvent polarity. The model derived from the analysis of linear spectra is adopted to predict nonlinear spectra and specifically hyper-Rayleigh scattering and two-photon absorption spectra. In polar solvents, the V-shaped chromophore is predicted to have a large HRS response in a wide spectral region (approximately 600-1300 nm). Anomalously large and largely solvent-dependent HRS responses for the linear chromophores are ascribed to symmetry lowering induced by polar solvation and amplified in this bulky system by the presence of two reaction fields.

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Section: Introductionmentioning

confidence: 99%

Spectroscopic Characterization and Modeling of Quadrupolar Charge-Transfer Dyes with Bulky Substituents

et al. 2012

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“…Absence of dipole moment reduces the tendency of these molecules to align in antiparallel pairs. Under an electric field, a random bulk of quadrupolar dyes can give rise to broad and red-shifted emission from a broken symmetry state . Therefore, the aggregation of these small molecules in a polymer matrix is dependent on the structural features of the matrix as well as the small molecule.…”

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“…Under an electric field, a random bulk of quadrupolar dyes can give rise to broad and red-shifted emission from a broken symmetry state. 16 Therefore, the aggregation of these small molecules in a polymer matrix is dependent on the structural features of the matrix as well as the small molecule. PVDF-TrFE provides a unique platform for delineating the features responsible for aggregation due its temperature-dependent FE properties.…”

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Ferroelectric Polymer Matrix for Probing Molecular Organization in Perylene Diimides

Chellappan

Kandappa

Rajaram

et al. 2014

J. Phys. Chem. Lett.

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Ferroelectric films of poly(vinylidene fluoride-co-trifluoroethylene) (PVDF-TrFE) provide a controlled environment to study the aggregation tendency of functional molecules such as perylene diimides (PDIs). The local electric field and free volume confinement parameters offered by the matrix are tailored to study the organizational and assembly characteritics of molecular acceptors. The optical properties of planar and nonplanar PDIs in the ferroelectric polymer matrix were studied systematically over a wide range that encompassed the ferroelectric transition temperature. This approach provides valuable insight into the properties of molecular materials used in applications ranging from bulk heterostructure-based photovoltaics to nonlinear optical materials.

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Multichromophoric Calix[4]arenes: Effect of Interchromophore Distances on Linear and Nonlinear Optical Properties

et al. 2012

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Multichromophoric calix[4]arenes with two or four disperse red one (DR1) moieties linked to the lower rim have been synthesized. The second-order nonlinear optical activity was measured by using the electric-field-induced second-harmonic generation technique and there was a nearly linear increase of the μβ value with the number of chromophores in the molecule without affecting the charge-transfer absorption wavelength. The effect that the number of DR1 units plays on the hyperpolarizability, the dipole moment, and the absorption maxima has been also studied by using quantum chemical calculations. It was found that it was necessary to synthesize multichromophores with distant chromophores to obtain large nonlinear optical responses.

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Quadrupolar Chromophores for Voltage Sensing and White‐Light Generation

Cited by 6 publications

References 16 publications

Spectroscopic Characterization and Modeling of Quadrupolar Charge-Transfer Dyes with Bulky Substituents

Spectroscopic Characterization and Modeling of Quadrupolar Charge-Transfer Dyes with Bulky Substituents

Ferroelectric Polymer Matrix for Probing Molecular Organization in Perylene Diimides

Multichromophoric Calix[4]arenes: Effect of Interchromophore Distances on Linear and Nonlinear Optical Properties

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