Synthesis and electronic spectra of novel merocyanine dyes bearing a maleimide ring incorporated into the methine chains

Shigemitsu, Yasuhiro; Sugimoto, Manabu; Itonaga, Sachiko; Komiya, Kaori; Tominaga, Yoshinori

doi:10.1016/s0143-7208(02)00143-2

Cited by 6 publications

(9 citation statements)

References 29 publications

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“…Vacuo-TD-DFT(B3LYP)6-31+G//Vacuo-DFT(B3LYP) 6-311G(2d,2p) gave 475 nm with a considerable λ max gap by 36 nm in comparison with PCM-TD-DFT(B3LTP)6-31+G//Vacuo-DFT(B3LYP)6-311G(2d,2p) (not in the Tables), which means that direct electronic perturbation play a dominant role in solvent effect. In our previous TD-DFT study for another series of maleimide derivatives [6][7], geometry optimizations including solvent effects were not performed. This is qualitatively rationalized including only direct electronic effect.…”

Section: Compound 3a: Assessment Of Td-dft Methodology and The Electrmentioning

confidence: 99%

“…The theoretical peaks computed were diverse and seemed to be non-systematic. In our previous study [6][7], a local density functional (SVWN) and a pure GGA functional (BPW91) outperformed a standard hybrid B3LYP functional which predicted severely shorter λ max than that of SVWN and BPW91. In the present study, qualitatively bathochromic shifts were computed in the order PBE0, MPW91PW91<B3LYP, B3PW91<O3LYP.…”

Section: Substituted Maleimides 3b-h 4a-h 5a-b and 6a-bmentioning

confidence: 96%

“…Through the extensive study on ketene dithioacetals utilized for heterocyclic synthesis [3,4], we have explored a wide utility of the functionalized maleimides which serve as active electrophilic reagents to afford fused pyridazine derivatives [5] and polymethine dyes [6][7]. The new dyes studied in this article comprise two key building-blocks; an electron-donating indolizine moiety and an electron-drawing maleimide ring.…”

Section: Introductionmentioning

confidence: 99%

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TD-DFT investigation on the electronic spectra of novel N-methylmaleimides linked with indolizine ring system

Shigemitsu

Komiya

Mizuyama

et al. 2008

Journal of Molecular Structure: THEOCHEM

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The major electronic absorption features in visible region were computationally investigated for a series of novel N-methylmaleimide derivatives. The newly synthesized compounds through the reaction of indolizines with N-methylmaleimides exhibited their maxima ranging 587-634 nm in solution at room temperature. Time dependent density functional theory (TD-DFT) calculations were performed in order to elucidate their structure-color relationship, as well as to assess its performance using a variety of exchange-correlation (XC) functionals and basis sets. 4-(indolizin-3-yl)-1-methyl-2,5-dioxo-1H-pyrrole-3-carbonitrile (referred to 3a hereafter), a representative of the new compounds, was analyzed in detail on its intramolecular push-pull electronic structure. As a consequence of systematic evaluation of computational strategies for 3a, we found that the theoretical λ max obtained by PCM-TDDFT/6-31+G(d,p)//DFT/6-311G(2d,2p) level of theory, which was consistently employed throughout this study, has converged within 2 nm deviation from λ max of the most elaborated level considered. Among some of the molecules with near-planarity structure, unusual discrepancies between the theoretical and the experimental λ max were observed, which should be attributed to the well-known TD-DFT limitation to describe multi-configurational or charge transfer (CT) excitations.

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Section: Compound 3a: Assessment Of Td-dft Methodology and The Electrmentioning

confidence: 99%

Section: Substituted Maleimides 3b-h 4a-h 5a-b and 6a-bmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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TD-DFT investigation on the electronic spectra of novel N-methylmaleimides linked with indolizine ring system

Shigemitsu

Komiya

Mizuyama

et al. 2008

Journal of Molecular Structure: THEOCHEM

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“…We have explored the abundant synthetic potential of the new functionalized maleimides which can effectively be converted to fused pyridazine derivatives [2] and polymethine dyes [3,4]. Herein we report the new series of dyes bearing push (pyrrole, indole)-pull (maleimide) systems.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and TDDFT Investigation of New Maleimide Derivatives Bearing Pyrrole and Indole Ring

Shigemitsu

Komiya

Mizuyama

et al. 2009

Research Letters in Organic Chemistry

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A novel series of heterocycles were obtained through the condensation reaction of 4-methylthiomaleimides with pyrroles and indoles. The newly synthesized compounds exhibit their major electronic absorption peaks ranging 435-504 nm in solution at room temperature. Time-dependent density-functional theory (TDDFT) calculations were systematically performed in order to elucidate their structure-color relationships, using a set of exchange-correlation (XC) functionals. The TDDFT computational scheme employing PCM-TDDFT/6-31+G(d,p)//DFT/6-311G(d,p) level of theory gave qualitatively satisfactory results in their λ max predictions.

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“…1. We furthermore explored the wider utility of the functionalized maleimides (5a,b) which serve as active electrophilic reagents to afford fused pyridazine derivatives [7] and polymethine dyes [8].…”

Section: Introductionmentioning

confidence: 99%

Reaction of functionalized maleimides with versatile nucleophiles. Synthesis, electronic spectra and molecular orbital study

et al. 2007

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Synthesis and electronic spectra of novel merocyanine dyes bearing a maleimide ring incorporated into the methine chains

Cited by 6 publications

References 29 publications

TD-DFT investigation on the electronic spectra of novel N-methylmaleimides linked with indolizine ring system

TD-DFT investigation on the electronic spectra of novel N-methylmaleimides linked with indolizine ring system

Synthesis and TDDFT Investigation of New Maleimide Derivatives Bearing Pyrrole and Indole Ring

Reaction of functionalized maleimides with versatile nucleophiles. Synthesis, electronic spectra and molecular orbital study

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