Electronic spectra and (hyper)polarizabilities of ketocyanine dye complexes with metal ions

Das, Mousumi; Sardar, Sanjib Kr; Bagchi, Sanjib

doi:10.1016/j.molstruc.2012.10.042

Cited by 3 publications

(6 citation statements)

References 30 publications

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“…The observed change in the bond length indicates that the percent contribution of the 'VB-CT' form increases due to protonation at the carbonyl O centre of the dyes. Similar observations have been reported for similar dyes undergoing complexation with metal ions at the carbonyl O centre [24,26]. Table 1.…”

Section: Effect Of Protonationsupporting

confidence: 86%

“…The presence of proton causes a decrease in the bond length of single bonds (NeC 2 , C 3 eC 4 and C 5 eC 6 ) whereas an increase in the same for double bonds (C 2 eC 3 , C 4 eC 5 and C 6 eO) is observed. Such an increase in the carbonyl bond length (C 6 eO) has also been found when the dye forms complex with metal ions [26,34]. Structure of such dyes can be represented as a resonance hybrid of two valence bond structures, namely, the 'neutral' and the valence bond charge transfer (VB-CT) form of the dyes [35,36].…”

Section: Effect Of Protonationmentioning

confidence: 90%

“…In order to include the effect of specific interaction, we have adopted a method described earlier by our group [26]. For the solvents where hydrogen bonding is important, namely, water, methanol, ethanol, we have initially optimised the dyeesolvent complex (solvent molecule placed at the carbonyl oxygen centre of the dyes (Fig.…”

Section: Effect Of Solvent On Optical Absorption Of the Dyesmentioning

confidence: 99%

“…A considerable of amount of research is in progress in designing molecule based materials with large non-linear optical responses (NLO) [21e25]. Previous calculation on donoreacceptor merocyanines and its metal ion complexes indicate that they possess significant first hyperpolarizability and are thus promising in field of NLO [26]. Ketocyanine and merocyanine compounds have also been used as laser dyes and have found application in polymer imaging systems [27,28].…”

Section: Introductionmentioning

confidence: 99%

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Electronic spectra and hyperpolarizabilities of structurally similar donor–acceptor dyes. A density functional theory analysis

Sarkar

Das

Bagchi

2015

Journal of Molecular Structure

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Section: Effect Of Protonationsupporting

confidence: 86%

Section: Effect Of Protonationmentioning

confidence: 90%

Section: Effect Of Solvent On Optical Absorption Of the Dyesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Electronic spectra and hyperpolarizabilities of structurally similar donor–acceptor dyes. A density functional theory analysis

Sarkar

Das

Bagchi

2015

Journal of Molecular Structure

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“…[1][2][3][4][5][6] A third class of molecules, ketocyanines ( Figure 1c), has features that resemble both the cyanines and the merocyanines. [7][8][9][10][11] The charge transfer resonance formso ft he ketocyanines clearly resemble the symmetrical electronic delocalization of cyanines, while the donor-acceptor functional group feature is merocyanine-like. We were interested in identifying whether it is possible to predictably bias the ketocyanine-type molecules to exhibit either of thesec haracteristics.W ep resent our initial findings here.It is reasonablet oa scertain that the electronic delocalization in ketocyanines will depend on the donor functional group's ability to stabilizet he positive charge ( Figure 2a).…”

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confidence: 96%

Effective Tuning of Ketocyanine Derivatives through Acceptor Substitution

Poe

Pelle

Byrnes

et al. 2015

Chemistry A European J

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A series of ketocyanine derivatives possessing bis(diarylamino)fluorenyl donors and variable acceptors installed at the bridging carbon atom were synthesized to investigate how the electronic structure of the dye can be systemically tuned through stabilization of the cyanine-like character of the donor by increasing the acceptor strength. Analysis of the (1) H NMR spectra indicates that the "charge-separated" species dominates in these dyes, given that carbons possessing a positive or negative charge in the resonance structures of this state purposefully shift downfield or upfield, respectively, depending on the strength of the acceptor moiety. In DAA-Fl-PI, the acceptor strength and the gain of acceptor aromaticity indicates a predisposition of the separated state, indicated by asymmetry in the (1) H NMR spectrum, as well as uneven distribution of the HOMO on the fluorenyl donor.

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Linear and nonlinear optical properties of V-shaped D–π–A–π–D chromophores: effects of the incorporation of aromatic rings in the polyenic π-bridges of open-chain ketocyanines

Momicchioli

Ponterini

Vanossi

2014

Phys. Chem. Chem. Phys.

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Following previous studies on α and β polarizabilities of ketocyanines, a subgroup of D-π-A-π-D quadrupolar chromophores with moderately V-shaped structure, the present work analyses the effects of modifying the π-bridges connecting the D (NMe2) and A (CO) groups. This aim is pursued through a detailed comparison between the previously studied ketocyanines (KC2, KC3) and a Michler's ketone analogue (KM1) bearing styrenic (in the place of polyenic) π-bridges. First, we report a spectroscopic study, including absorption and fluorescence anisotropy spectra, aimed to probe the electronic peculiarities of KM1 as well as to derive consistent three-state model (TSM) parameters for the three compounds. The paper goes on with an extensive theoretical study, carried out in the framework of the density functional theory (DFT), encompassing the structure, the electronic spectrum, α and β polarizabilities and two-photon absorption (TPA) cross-sections (σTP). Calculations performed according to the sum-over-states (SOS) approach are discussed with reference to the performances of few-state descriptions, it is shown that such descriptions (including TSM), which have been proved to be quite reliable in the case of KC2 and KC3, lose their effectiveness with KM1 because of the electronic characteristics related to the styrenic π-bridges. As to the TPA cross-sections, the results of TSM and SOS approaches concerning the TSM g → c and g → e transitions are supplemented by those obtained using the quadratic response theory. A common qualitative conclusion, traceable to the degree of bending of the V-shaped structure, is that in the case of KM1 the allowed (g → e) and the "forbidden" (g → c) transitions both should be observable in the TPA spectrum, as confirmed by experiment.

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Electronic spectra and (hyper)polarizabilities of ketocyanine dye complexes with metal ions

Cited by 3 publications

References 30 publications

Electronic spectra and hyperpolarizabilities of structurally similar donor–acceptor dyes. A density functional theory analysis

Electronic spectra and hyperpolarizabilities of structurally similar donor–acceptor dyes. A density functional theory analysis

Effective Tuning of Ketocyanine Derivatives through Acceptor Substitution

Linear and nonlinear optical properties of V-shaped D–π–A–π–D chromophores: effects of the incorporation of aromatic rings in the polyenic π-bridges of open-chain ketocyanines

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