- Synthesis and characterization of spin-coatable tert-amine molecules for hole-transport in organic light-emitting diodes
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The synthesis of two tert-amine-based, non-fluorescent, hole-transport molecules (4,4′-[bis-{(4-di-n-hexylamino)benzylideneamino)]stilbene (DHABS) and 4,4′-[bis-{(4-diphenylamino)benzylideneamino}]stilbene) (DPABS) that are suitable for spin coating on in
- Mishra,Nayak,Ray,Patankar,Narasimhan,Periasamy
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- A self-assembled nanohybrid composed of fluorophore-phenylamine nanorods and Ag nanocrystals: Energy transfer, wavelength shift of fluorescence and TPEF applications for live-cell imaging
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A fluorophore-phenylamine derivative (L) has been coupled with silver nanocrystals (NCs) to construct an L-Ag nanohybrid. Owing to synergic effects of the L and Ag components, the exciton-plasmon interactions between L and Ag increase the strength of the
- Kong, Lin,Yang, Jia-Xiang,Li, Sheng-Li,Zhang, Qiong,Xue, Zhao-Ming,Zhou, Hong-Ping,Wu, Jie-Ying,Jin, Bao-Kang,Tian, Yu-Peng
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- Rational design, facile synthesis, and linear/nonlinear optical properties of novel two-photon absorption stilbene derivatives with different configurations
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Four novel two-photon absorption compounds (1MOBI, 2MOHA, 3BrBI, and 4BrHA), which have assembled stilbene π-bridge, different electron acceptors and donors, were synthesized conveniently via the one-step Horner-Wadsworth-Emmons reaction. Their configurations are A-π-D-π-A, D′-π-D-π-D′, A′-π-A-π-A′, and D-π-A-π-D, respectively. Their linear and nonlinear optical properties including linear absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence, were systematically investigated in various solvents. The results demonstrate that the compounds with dihexylamino donors exhibit good optical properties. 2MOHA and 4BrHA exhibit large two-photon absorption cross-sections (2183 and 1737 GM) in DMF, which are larger than those of many known stilbene derivatives. The relationships between the structures and the optical properties were studied aided with the time-dependent density functional theory calculations.
- Cai, Zhi-Bin,Dai, Huan,Li, Sheng-Li,Lou, Qiao-Xian,Tian, Yu-Peng
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- DHASPI aggregate bactericide and preparation method and application thereof
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The invention discloses a DHASPI aggregate bactericide and a preparation method and application thereof. The preparation method comprises the following steps: (1), preparing a solution with the concentration of 1-10mM as a DHASPI mother solution by using DHASPI as a solute and absolute ethanol as a solvent; (2), taking the DHASPI mother solution, and preparing a DHASPI solution with the concentration of 0.7-80[mu]M by using pure water as a solvent to obtain the DHASPI aggregate bactericide, wherein the DHASPI is an abbreviation for trans-4-[4-(dihexylamino)styryl]-1-methylpyridinium iodide. Experiments show that after the DHASPI aggregate bactericide is added into water, bacteria can be killed under a light irradiation condition.
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Paragraph 0026; 0030; 0034
(2019/08/20)
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- Linear and Nonlinear Optical Properties of Tricyanopropylidene-Based Merocyanine Dyes: Synergistic Experimental and Theoretical Investigations
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New merocyanines dyes with tricyanopropylidene-based acceptor units connected to dihexylaminophenyl or dihexylaminothiophenyl donor moieties through polyenic bridges of different lengths have been designed. All derivatives exhibited a strong dipolar character and showed a typical intramolecular charge transfer (ICT) transition. NMR spectroscopy experiments combined with DFT calculations demonstrated that both the nature of the donor–acceptor pair and the length of the conjugated linker strongly impact the electronic structure of the dyes and induce alteration in the bond-length alternation (BLA) and marked shifts in the ICT absorption bands. Hyper-Rayleigh scattering experiments revealed an exponential increase in the second-harmonic generation response as the polyenic chain length was increased. Strikingly, the largest chromophores with the strongest donor–acceptor pair exhibited a very high first hyperpolarizabilty together with a cyanine-like electronic structure, which apparently contradicts the paradigm of optimal BLA predicted by the two-state model. Although it decreased as the polyenic chain length increased, all dyes also exhibited high thermal stability, which demonstrates their potential for applications in nonlinear optical devices.
- Parthasarathy, Venkatakrishnan,Pandey, Ravindra,Das, Puspendu Kumar,Castet, Frédéric,Blanchard-Desce, Mireille
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p. 187 - 197
(2018/01/27)
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- Monocarboxylate transporter 1 inhibitors as potential anticancer agents
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Potent monocarboxylate transporter 1 inhibitors (MCT1) have been developed based on α-cyano-4-hydroxycinnamic acid template. Structure-activity relationship studies demonstrate that the introduction of p-N, N-dialkyl/diaryl, and o-methoxy groups into cyanocinnamic acid has maximal MCT1 inhibitory activity. Systemic toxicity studies in healthy ICR mice with few potent MCT1 inhibitors indicate normal body weight gains in treated animals. In vivo tumor growth inhibition studies in colorectal adenocarcinoma (WiDr cell line) in nude mice xenograft models establish that compound 27 exhibits single agent activity in inhibiting the tumor growth.
- Gurrapu, Shirisha,Jonnalagadda, Sravan K.,Alam, Mohammad A.,Nelson, Grady L.,Sneve, Mary G.,Drewes, Lester R.,Mereddy, Venkatram R.
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p. 558 - 561
(2015/05/27)
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- Relationship between molecular stacking and optical properties of 9,10-bis((4-N,N-dialkylamino)styryl) anthracene crystals: The cooperation of excitonic and dipolar coupling
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Five 9,10-bis((4-N,N-dialkylamino)styryl) anthracene derivatives (DSA-C1-DSA-C7) with different length alkyl chains were synthesized. They showed the same color in dilute solutions but different colors in crystals. The absorption, photoluminescence, and fluorescence decay indicate that there exist both excitonic and dipolar coupling in crystals of DSA-C1-DSA-C7. X-ray crystallographic analysis revealed that all the crystals belong to the triclinic space group P1 with one molecule per unit cell and that the molecules in every crystal have the identical orientation. This offers ideal samples to investigate the impact of the molecular stacking on the optical properties of the crystals. For the first time, the cooperation of excitonic and dipolar coupling has been comprehensively studied, and the contribution to the spectral shift from the excitonic and dipolar couplings quantitatively obtained. The experiments of amplified spontaneous emission (ASE) together with measurements of the quantum efficiency further confirmed this interpretation. The results suggest that the excitonic and dipolar couplings between the adjacent molecules are both important and jointly induce the spectral shifts of the crystals.
- Li, Feng,Gao, Na,Xu, Hai,Liu, Wei,Shang, Hui,Yang, Wenjun,Zhang, Ming
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p. 9991 - 9997
(2014/08/18)
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- Alkyl substituent effects on J- or H-aggregate formation of bisazomethine dyes
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Bisazomethine dyes with terminal alkyl substituents of different chain lengths (BAR: R = 1, 2, 3, 4, 5 and 6) were synthesized and deposited on a glass substrate to investigate the effect of the alkyl chain length on aggregate formation. Methyl- and ethyl-substituted bisazomethine dyes (BA1 and BA2) formed J-aggregates in thin films (ca. 50 nm), whereas, propyl-, butyl-, pentyl- and hexyl-substituted derivatives (BA3, BA4, BA5 and BA6) formed H-aggregates in thin films (ca. 50 nm). The aggregate formation of the BARs changed drastically between ethyl- and propyl-substituents (BA2/BA3). However, no remarkable changes were observed in the surface morphologies of BA2 and BA3 films. It is suggested that the critical determinant of aggregate formation of BAR is the molecular packing in the film, which depends on the chain length of the terminal alkyl substituent.
- Kinashi, Kenji,Lee, Kyun-Phyo,Matsumoto, Shinya,Ishida, Kenji,Ueda, Yasukiyo
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p. 783 - 788
(2012/02/05)
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- Two-photon absorption properties of proquinoidal D-A-D and A-D-A quadrupolar chromophores
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We report the synthesis, one- and two-photon absorption spectroscopy, fluorescence, and electrochemical properties of a series of quadrupolar molecules that feature proquinoidal p-aromatic acceptors. These quadrupolar molecules possess either donoracceptor donor (D-A-D) or acceptordonoracceptor (A-D-A) electronic motifs, and feature 4-N,N-dihexylaminophenyl, 4-dodecyloxyphenyl, 4-(N,N-dihexylamino)benzo[c][1,2,5]thiadiazolyl or 2,5-dioctyloxyphenyl electron donor moieties and benzo[c][1,2,5]thiadiazole (BTD) or 6,7-bis(30,70-dimethyloctyl)[1,2,5]thiadiazolo[3,4-g]quinoxaline (TDQ) electron acceptor units. These conjugated structures are highly emissive in nonpolar solvents and exhibit large spectral red-shifts of their respective lowest energy absorption bands relative to analogous reference compounds that incorporate phenylene components in place of BTD and TDQ moieties. BTD-based D-A-D and A-D-A chromophores exhibit increasing fluorescence emission redshifts, and a concomitant decrease of the fluorescence quantum yield (Ff) with increasing solvent polarity; these data indicate that electronic excitation augments benzothiadiazole electron density via an internal charge transfer mechanism. The BTD- and TDQcontaining structures exhibit blue-shifted two-photon absorption (TPA) spectra relative to their corresponding one-photon absorption (OPA) spectra, and display high TPA cross sections (>100 GM) within these spectral windows. D-A-D and A-D-A structures that feature more extensive conjugation within this series of compounds exhibit larger TPA cross sections consistent with computational simulation. Factors governing TPA properties of these quadrupolar chromophores are discussed within the context of a three-state model.
- Susumu, Kimihiro,Fisher, Jonathan A.N.,Zheng, Jieru,Beratan, David N.,Yodh, Arjun G.,Therien, Michael J.
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p. 5525 - 5539
(2011/08/06)
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- Two-photon absorbing materials with quenched emission
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The present invention provides substituted phenanthroline compounds with high two photon absorption cross sections, as well as substituted phenanthroline compounds which additionally have quenched fluorescence emission upon two photon absorption.
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Page/Page column 6
(2009/01/20)
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- Fluorophore compounds and their use in biological systems
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Fluorophore compounds and methods for their use are disclosed. The fluorophores contain a 2-dicyanomethylen-3-cyano-2,5-dihydrofuran (DCDHF) moiety and one or more donor groups conjugated to the 2-dicyanomethylen-3-cyano-2,5-dihydrofuran group. The donor
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- Novel dyes for the detection or quantification of desirable target molecules
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The present invention provides dyes, reactive dyes and labeled reagents that may be used in the detection or quantification of desirable target molecules, such as proteins and nucleic acids. Dyes are provided that may be used free in solution where the bi
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- Star-shaped push-pull compounds having 1,3,5-triazine cores
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The 1,3,5-triazines 9-11 having OPV chains in the 2-, 4- and 6-position represent star-shaped compounds which exhibit strong push-pull effects. Their long-wavelength absorption S0 → S1 is characterized by an intramolecular charge tra
- Meier, Herbert,Karpuk, Elena,Holst, Hans Christof
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p. 2609 - 2617
(2007/10/03)
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- Novel two-photon-absorbing, 1,10-phenanthroline-containing π-conjugated chromophores and their nickel(II) chelated complexes with quenched emissions
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Novel 1,10-phenanthroline-containing π-conjugated chromophores with varied electron donors were synthesized and characterized together with their corresponding nickel(II) chelated complexes. The linear absorption maxima for these chromophores could be tun
- Zheng, Qingdong,He, Guang S.,Prasad, Paras N.
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p. 579 - 587
(2007/10/03)
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- Design and synthesis of push-pull chromophores for second-order nonlinear optics derived from rigidified thiophene-based π-conjugating spacers
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Two series of push-pull chromophores built around thiophene-based π-conjugating spacers rigidified either by covalent bonds or by noncovalent intramolecular interactions have been synthesized and characterized by UV-vis spectroscopy, electric field induced second harmonic generation (EFISH) and differential scanning calorimetry. Comparison of the linear and second-order nonlinear optical properties of chromophores based on a covalently bridged dithienylethylene (DTE) spacer with those of their analogues based on open chain DTE shows that the rigidification of the spacer produces a considerable bathochromic shift of the absorption maximum together with a dramatic enhancement of the molecular quadratic hyperpolarizability (μΒ) which reaches values among the highest reported so far. A second series of NLO-phores has been derived from a 2,2′-bi(3,4-ethylenedioxythiophene) (BEDOT) π-conjugating spacer. As indicated by X-ray and UV-vis data, rigidification of the spacer originates in that case, from noncovalent intramolecular interactions between sulfur and oxygen atoms. Again, comparison with the parent compounds based on an unsubstituted bithiophene spacer reveals a marked red shift of the absorption maximum and a large enhancement of μΒ. In an attempt to distinguish the contribution of the electronic and geometrical effects of the ethylenedioxy group, a third series of NLO-phores based on 3,4-ethylenedioxythiophene (EDOT) and 3,4-dihexyloxythiophene spacers has been synthesized. Comparison with compounds based on unsubstituted thiophene shows that, despite a red shift ofλmax, introduction of alkoxy groups leads to a decrease of μΒ. Theoretical calculations indicate that this effect results from a decrease of the dipole moment (μ) caused by the auxiliary electron-donor alkoxy groups on the thiophene ring. In contrast, replacement of BT by BEDOT produces an increase of μ, which associated with the noncovalent rigidification of the BT system accounts for the observed enhancement of μΒ.
- Raimundo, Jean-Manuel,Blanchard, Philippe,Gallego-Planas, Nuria,Mercier, Nicolas,Ledoux-Rak, Isabelle,Hierle, Rolland,Roncali, Jean
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p. 205 - 218
(2007/10/03)
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- Quinolinium- and pyridinium-based fluorescent dye compounds
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The present invention relates to quinolinium- and pyridinium-based fluorescent dyes. The dyes are useful for staining proteins in solution, in gels and on solid supports. The dyes of the invention exhibit higher fluorescence emission than known compounds when bound to proteins and also exhibit improved contrast of fluorescence intensity between their protein-bound and unbound states.
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- Quinolinium- and pyridinium-based fluorescent dye compounds
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The present invention relates to quinolinium- and pyridinium-based fluorescent dyes. The dyes are useful for staining proteins in solution, in gels and on solid supports. The dyes of the invention exhibit higher fluorescence emission than known compounds
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- Extended conjugation in stilbenylsquaraines
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Unsymmetrical 1-aryl-3-stilbenylsquaraines 2a-e and 1,3-bis(stilbenyl)squaraines 3a-c were prepared by CC coupling reactions of the corresponding substituted arenes with derivatives of squaric acid (Schemes 2 and 3). Dialkylamino and alkoxy groups enhance the solubility of these dyes and enlarge the intramolecular charge transfer of these donor-acceptor-donor systems. The extended conjugation of the stilbene units - in comparison with arene building blocks - leads to significant bathochromic shifts in the Vis/NIR absorption spectra.
- Meier, Herbert,Petermann, Ralf,Dullweber, Uta
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experimental part
p. 744 - 754
(2011/10/12)
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- Charge-Shift Probes of Membrane Potential. Synthesis
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We are reporting two general synthetic approaches to a number of (aminostyryl)pyridinium dyes and their heterocyclic analogues which are of interest as electrochromic probes for membrane potential.The two routes which involve palladium-catalyzed coupling or aldol condensation permit considerable structure variations to be introduced in the dyes.Some spectral properties of the dyes are discussed.
- Hassner, A.,Birnbaum, D.,Loew, L. M.
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p. 2546 - 2551
(2007/10/02)
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