Contrasting Solvent Polarity Effect on the Photophysical Properties of Two Newly Synthesized Aminostyryl Dyes in the Lower and in the Higher Solvent Polarity Regions

Shaikh, Mhejabeen; Mohanty, Jyotirmayee; Singh, Prabhat; Bhasikuttan, Achikanath C.; Rajule, Rajkumar N.; Satam, Vijay; Bendre, Ratnamala S.; Kanetkar, V. R.; Pal, Haridas

doi:10.1021/jp9107969

Cited by 75 publications

(36 citation statements)

References 73 publications

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“…Figure 4 shows the plots of the 0-0 transition energy and FWHM as a solvent polarity factor, P f = ( ε −1)/( ε +2)−( n 2 −1)/( n 2 +2). This parameter can be derived to combine the Lippert and Mataga equation51 and the effect of elliptical cavity formed by the surrounding solvent molecules 52. It is appropriately applicable for the case of carotenoids to explain the solvent dependent energy-shift of optical absorption 10,52.…”

Section: Resultsmentioning

confidence: 99%

Femtosecond Transient Absorption Spectroscopic Study of a Carbonyl-Containing Carotenoid Analogue, 2-(all-trans-Retinylidene)-indan-1,3-dione

et al. 2011

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The photophysical properties of a carbonyl-containing carotenoid analogue in an s-cis configuration, relative to the conjugated π system, 2-(all-trans-retinylidene)-indan-1,3-dione (C20Ind), were investigated by femtosecond time-resolved spectroscopy in various solvents. The lifetime of the optically forbidden S 1 state of C20Ind becomes long as solvent polarity increases. This trend is completely opposite to the situation of S 1-ICT dynamics of carbonyl-containing carotenoids, such as peridinin and fucoxanthin. Excitation energy dependence of the transient absorption measurements shows that the transient absorption spectra in non-polar solvents were originated from two distinct transient species, while those in polar and protic solvents are due to a single transient species. By referring to the results of MNDO-PSDCI (modified neglect of differential overlap with partial single-and double-configuration interaction) calculations, we conclude: (1) In polar and protic solvents, the S 1 state is generated following excitation up to the S 2 state; (2) In non-polar solvents, however, both the S 1 and 1 nπ * states are generated; and (3) C20Ind does not generate the S 1-ICT state, despite the fact that it has two conjugated carbonyl groups.

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Section: Resultsmentioning

confidence: 99%

Femtosecond Transient Absorption Spectroscopic Study of a Carbonyl-Containing Carotenoid Analogue, 2-(all-trans-Retinylidene)-indan-1,3-dione

et al. 2011

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“…[1][2][3][4][5] However, the nonemissive ICT state and single emission only from the ICT state were also observed in few cases. [6][7][8][9][10] Though several mechanisms were proposed to explain the origin of dual fluorescence in p-(N,N-dimethylamino)benzonitrile (1) …”

Section: Introductionmentioning

confidence: 99%

The role of hydrogen bonding in excited state intramolecular charge transfer

Chipem

Mishra

Krishnamoorthy

2012

Phys. Chem. Chem. Phys.

170

133

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Intramolecular charge transfer (ICT) that occurs upon photoexcitation of molecules is a vital process in nature and it has ample applications in chemistry and biology. The ICT process of the excited molecules is affected by several environmental factors including polarity, viscosity and hydrogen bonding. The effect of polarity and viscosity on the ICT processes is well understood. But, despite the fact that hydrogen bonding significantly influences the ICT process, the specific role of hydrogen bonding in the formation and stabilization of the ICT state is not unambiguously established. Some literature reports predicted that the hydrogen bonding of the solvent with a donor promotes the formation of a twisted intramolecular charge transfer (TICT) state. Some other reports stated that it inhibits the formation of the TICT state. Alternatively, it was proposed that the hydrogen bonding of the solvent with an acceptor favors the TICT state. It is also observed that a dynamic equilibrium is established between the free and the hydrogen bonded ICT states. This perspective focuses on the specific role played by hydrogen bonding of the solvent with the donor and the acceptor, and by proton transfer in the ICT process. The utility of such influence in molecular recognition and anion sensing is discussed with a few recent literature examples in the end.

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“…13 Studies of donor-acceptors systems with olefinic bonds have attracted widespread interest, because in many photochemical and photobiological systems photoisomerization and ICT compete with each other. [14][15][16][17][18][19][20][21][22] In addition, these push-pull systems are promising compounds for optical materials. Since they are highly polarizable, they are potential materials for nonlinear optics, harmonic generation, optical limitation, twophoton absorption, and imaging of biological materials.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced intramolecular charge transfer in trans-2-[4′-(N, N-dimethylamino)styryl]imidazo[4,5- b]pyridine: effect of introducing a C=C double bond

Mishra

Sahu

Tripathi

et al. 2014

Photochem Photobiol Sci

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The spectral characteristics of trans-2-[4'-(N,N-dimethylamino)styryl]imidazo[4,5-b]pyridine (t-DMASIP-b) have been investigated using absorption and fluorescence techniques, and compared with 2-(4'-N,N-dimethylamino)imidazo[4,5-b]pyridine (DMAPIP-b). The study reveals that introduction of a C[double bond, length as m-dash]C double bond strongly perturbs the photophysics of the system. Unlike DMAPIP-b, t-DMASIP-b emits a single emission in aprotic and protic solvents. The emission occurs from the locally excited state in nonpolar solvents and from a planar intramolecular charge transfer (PICT) state in polar solvents. Multiple linear regression analysis suggests that among the different solvent parameters, the dipolar interaction contributes more to the stabilization of the system in both the ground and excited states. Theoretical calculations suggest that, unlike in DMAPIP-b, proton coupled twisted intramolecular charge transfer (TICT) emission does not occur in t-DMASIP-b. The higher quantum yield obtained in the viscous solvent glycerol is attributed to the restriction of the twisting of the olefinic bond. The photoirradiation of t-DMASIP-b shows that isomerization takes place in all solvents, including viscous glycerol. The theoretically simulated potential energy surface shows that isomerization occurs via a phantom state, which is a nonradiative process. The rise in temperature favors the photoisomerization, thus, the fluorescence quantum yield decreases. The prototropic study indicates that, unlike in DMAPIP-b, the protonation takes place at different places to form the monocations.

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Contrasting Solvent Polarity Effect on the Photophysical Properties of Two Newly Synthesized Aminostyryl Dyes in the Lower and in the Higher Solvent Polarity Regions

Cited by 75 publications

References 73 publications

Femtosecond Transient Absorption Spectroscopic Study of a Carbonyl-Containing Carotenoid Analogue, 2-(all-trans-Retinylidene)-indan-1,3-dione

Femtosecond Transient Absorption Spectroscopic Study of a Carbonyl-Containing Carotenoid Analogue, 2-(all-trans-Retinylidene)-indan-1,3-dione

The role of hydrogen bonding in excited state intramolecular charge transfer

Photoinduced intramolecular charge transfer in trans-2-[4′-(N, N-dimethylamino)styryl]imidazo[4,5- b]pyridine: effect of introducing a C=C double bond

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