New quadrupolar fluorophores with high two-photon excited fluorescence

Ventelon, Lionel; Blanchard‐Desce, Mireille; Moreaux, Laurent; Mertz, Jérôme

doi:10.1039/a906182g

Cited by 174 publications

(118 citation statements)

References 17 publications

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“…(1(1)-1'(4))+(1 (1) [117] four lowest excited states of π conjugated systems were theoretically investigated using using the ab initio response theory. The materials were synthesized and characterized by Kim et al [123] and Ventelon et al [122] Agren et al showed that their theoretical findings were consistent with the correlation between large 2PA crosssections and a π center. Although 1PA spectra were strongly correlated to the molecular length, this was not always the case for 2PA in the visible domain [117].…”

Section: ∆E Evmentioning

confidence: 68%

“…A types with the aim of increasing 2PA absorption cross-sections [118][119][120][121][122][123]. However, the choice of functional groups and linkages, the most appropriate for developing chromophores with large 2PA characteristics, is still under active investigation [124][125][126][127][128][129][130][131][132][133][134][135].…”

Section: D-π-a D-π-d or A-π-a Molecular Structures Have Been Propmentioning

confidence: 99%

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Theory and computations of two-photon absorbing photochromic chromophores

Masunov

Михайлов

2010

Eur. J. Chem.

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KEYWORDSExponential growth in information technology generates ever increasing amounts of data, making recording density of the storage media crucially important. Two-photon absorption was proposed as a basis for high-density multi-layer technology for optical memory and logic devices. This technology suggests to use polymers, doped with photochromic compounds that undergo a reversible photoinduced isomerization, or photoswitching. In this review we consider recent theoretical works and benchmarking studies of the DFT-based methods, capable to predict two-photon absorption (2PA) and photochemical activity, Next we review the applications of these methods to design a prototype molecule that combines the photonmode recording property of photochromic compounds with large 2PA cross-section. We conclude that a posteriori Tamm-Dancoff approximation to the second order CEO approach in Density Functional Theory is the powerful tool for both quantitative predictions and qualitative understanding of the excited state processes in photophysics and photochemistry. We also emphasize general principles for the rational design of a two-photon operated photoswitch.TDDFT Organic photochemistry Photocyclization Photoinduced reactions Two-photon absorption State-to-state transition dipoles

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Section: ∆E Evmentioning

confidence: 68%

Section: D-π-a D-π-d or A-π-a Molecular Structures Have Been Propmentioning

confidence: 99%

Theory and computations of two-photon absorbing photochromic chromophores

Masunov

Михайлов

2010

Eur. J. Chem.

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“…In the quest of improving NLO properties, attention has been essentially focused on dipolar molecules for several decades. [1][2][3] More recently, quadrupolar systems have been designed and investigated [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] and have shown improved properties, in particular with respect to the trade-off between optical transparency and NLO performance. Lately, attention has turned toward multipolar [22][23][24][25][26][27][28][29][30][31][32][33] and branched structures including dendrimers.…”

Section: Introductionmentioning

confidence: 99%

Effects of (Multi)branching of Dipolar Chromophores on Photophysical Properties and Two-Photon Absorption

et al. 2005

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To investigate the effect of branching on linear and nonlinear optical properties, a specific series of chromophores, epitome of (multi)branched dipoles, has been thoroughly explored by a combined theoretical and experimental approach. Excited-state structure calculations based on quantum-chemical techniques (timedependent density functional theory) as well as a Frenkel exciton model nicely complement experimental photoluminescence and one-and two-photon absorption findings and contribute to their interpretation. This allowed us to get a deep insight into the nature of fundamental excited-state dynamics and the nonlinear optical (NLO) response involved. Both experiment and theory reveal that a multidimensional intramolecular charge transfer takes place from the donating moiety to the periphery of the branched molecules upon excitation, while fluorescence stems from an excited state localized on one of the dipolar branches. Branching is also observed to lead to cooperative enhancement of two-photon absorption (TPA) while maintaining high fluorescence quantum yield, thanks to localization of the emitting state. The comparison between results obtained in the Frenkel exciton scheme and ab initio results suggests the coherent coupling between branches as one of the possible mechanisms for the observed enhancement. New strategies for the rational design of NLO molecular assemblies are thus inferred on the basis of the acquired insights.

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“…Aside from the donor-acceptor configuration of 2PA active chromophores, it was also established by Bredas et al that increasing the length and charge transfer of the molecules results in an increase in 2PA crossections and may also result in a significant shift of 2PA to longer wavelengths [6]. Complementarily, Agren et al theoretically studied four lowest excited states of π conjugated systems experimentally produced and characterized by Kim et al [10] and Ventelon et al [9] using ab initio response theory. They showed that their theoretical findings were consistent with the correlation between large 2PA crossections and a π center, but that though the one photon absorption (1PA) spectra was strongly correlated to the molecular length this was not always the case for 2PA in the visible domain [5].…”

Section: D-π-a D-π-d Ormentioning

confidence: 99%

“…In recent studies fluorene derivatives have been extended to D-π-π-A and A-π-π-A types with the aim of increasing 2PA absorption cross-sections [6][7][8][9][10]. However, the choice of functional groups and linkages the most appropriate for developing chromophores with the largest 2PA characteristics it is still under active investigation.…”

Section: D-π-a D-π-d Ormentioning

confidence: 99%

Predictions of Two Photon Absorption Profiles Using Time-Dependent Density Functional Theory Combined with SOS and CEO Formalisms

Tafur¹,

Михайлов²,

Belfield

et al. 2009

Lecture Notes in Computer Science

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Abstract. Two-photon absorption (2PA) and subsequent processes may be localized in space with a tightly focused laser beam. This property is used in a wide range of applications, including three dimensional data storage. We report theoretical studies of 5 conjugated chromophores experimentally shown to have large 2PA cross-sections. We use the Time Dependent Density Functional Theory (TD-DFT) to describe the electronic structure. The third order coupled electronic oscillator formalism is applied to calculate frequency-dependent second order hyperpolarizability. Alternatively, the sum over states formalism using state-to-state transition dipoles provided by the a posteriori Tamm-Dancoff approximation is employed. It provides new venues for qualitative interpretation and rational design of 2PA chromophores.

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New quadrupolar fluorophores with high two-photon excited fluorescence

Abstract: New quadrupolar fluorophores that exhibit enhanced twophoton excited fluorescence were designed according to a molecular engineering approach based on push-push and pull-pull elongated molecules built from a rigid conjugated core (either dihydrophenanthrene or dithienothiophene).

Cited by 174 publications

References 17 publications

Theory and computations of two-photon absorbing photochromic chromophores

Theory and computations of two-photon absorbing photochromic chromophores

Effects of (Multi)branching of Dipolar Chromophores on Photophysical Properties and Two-Photon Absorption

Predictions of Two Photon Absorption Profiles Using Time-Dependent Density Functional Theory Combined with SOS and CEO Formalisms

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