New one- and two-dimensional 4H-pyranylidene NLO-phores

Andreu, Raquel; Carrasquer, Laura; Garı́n, Javier; Modrego, María Jesús; Orduna, Jesús; Alicante, Raquel; Villacampa, Belén; Allain, Magali

doi:10.1016/j.tetlet.2009.03.197

Cited by 29 publications

(28 citation statements)

References 35 publications

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“…Many different structures of electron donor fragments are introduced (compounds 45-57 in Fig.13) in the pyranylidene backbone after introducing the electron acceptor fragment [1,[4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][27][28][29]31]. In cases where only one methyl group reacts with the aldehyde, a mono-styryl derivative of pyranylidene is obtained (see Fig.13).…”

Section: Synthesis Of Pyranilydene and Isophorene Type Red Luminescenmentioning

confidence: 99%

Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

Zariņš¹,

Vembris²,

Kokars³

et al. 2012

Organic Light Emitting Devices

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Section: Synthesis Of Pyranilydene and Isophorene Type Red Luminescenmentioning

confidence: 99%

Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

Zariņš¹,

Vembris²,

Kokars³

et al. 2012

Organic Light Emitting Devices

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“…For the synthesis of the title compound, see: Peng et al (2006). For background to luminescent materials, see: Andreu et al (2009); Kim et al (2004); Yao et al (2006a,b).…”

Section: Related Literaturementioning

confidence: 99%

“…Indene-1,3(2H)-dione moiety is used as a strong electron acceptor for luminescent materials such as organic lightemitting diodes (OLED) (Yao et al, 2006a,b;Andreu et al, 2009;Kim et al, 2004). For the purpose of finding a pHsensing luminescent dye, we designed the title compound which includes indene-1,3(2H)-dione moiety conjugated with 1,4-dihydropyridine ring possessing a 4-hydroxystyryl group.…”

Section: S1 Commentmentioning

confidence: 99%

(E)-2-{2-tert-Butyl-6-[2-(4-hydroxyphenyl)ethenyl]-1-propyl-1,4-dihydropyridin-4-ylidene}indane-1,3-dione

Park

Kim

2010

Acta Cryst E

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The title compound, C29H29NO3, the nearly planar nine-membered indanedione ring [maximum deviation = 0.027 (2) Å] is located approximately parallel to its carrier pyridine ring [maximum deviation = 0.021 (2) Å] with a dihedral angle of 1.8 (1)° between the planes. However, because of steric hindrance, the benzene ring [maximum deviation = 0.006 (2) Å] is not parallel to the pyridine ring [dihedral angle = 37.29 (8)°]. The molecules display numerous intermolecular π–π interactions between the five- and six-membered rings, the shortest centroid–centroid distance being 3.796 (2) Å. There are inter- and intramolecular O—H⋯O and C—H⋯O hydrogen bonds.

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“…However, when these moieties are coupled using the strong phenyl isoxazolone acceptor,t he electron density distribution is akin to ad onor-acceptor molecule, that is, merocyanines.Among the molecules shown in Figure 2b,t he acceptor strength increases with the following trend:k etone < malononitrile (CN) < 1,3-indandione (In) < 1,3-dimethylbarbituric acid (6O) < 1,3-diethyl-2-thiobarbituric acid (6S) < 3-phenyl-5-isoxazolone (PI). [15][16][17][18][19][20] DAA-Fl was synthesized according to ap reviously published procedure. [21] Briefly,3 ,6-dibromo-9H-fluoren-9one was synthesized from the bromination and subsequent ring contraction of phenanthrene-9,10-dione.…”

mentioning

confidence: 99%

“…Among the molecules shown in Figure 2b,t he acceptor strength increases with the following trend:k etone < malono- [15][16][17][18][19][20] DAA-Fl was synthesized according to ap reviously published procedure. [21] Briefly,3 ,6-dibromo-9H-fluoren-9one was synthesized from the bromination and subsequent ring contraction of phenanthrene-9,10-dione.…”

mentioning

confidence: 99%

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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New one- and two-dimensional 4H-pyranylidene NLO-phores

Cited by 29 publications

References 35 publications

Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

(E)-2-{2-tert-Butyl-6-[2-(4-hydroxyphenyl)ethenyl]-1-propyl-1,4-dihydropyridin-4-ylidene}indane-1,3-dione

Effective Tuning of Ketocyanine Derivatives through Acceptor Substitution

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