Palladium-Catalyzed Synthesis of trans-4-(N,N-Bis(2-pyridyl)amino)stilbene. A New Intrinsic Fluoroionophore for Transition Metal Ions

Yang, Jye‐Shane; Lin, and Yu-Hsi; Yang, Ching‐Sheng

doi:10.1021/ol017260l

Cited by 48 publications

(33 citation statements)

References 20 publications

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“…The synthesis of 5,5'-bis(di-p-anisylamino)-2,2'-bipyridine (1) has been reported [17] previously by palladiumcatalyzed C À N coupling between 5,5'-dibromo-2,2'-bipyridine [19] and 4,4'-dimethoxydiphenylamine. [20] A single crystal was obtained by slow evaporation of the solvent of a solution of 1 in CHCl 3 , and its X-ray crystallographic structure is shown in Figure 3. [21] The NÀN distance between the two amino nitrogen atoms is 9.80 .…”

Section: Resultsmentioning

confidence: 99%

Electronic Coupling between Two Amine Redox Sites through the 5,5′‐Positions of Metal‐Chelating 2,2′‐Bipyridines

Nie

Chen

Yao

et al. 2012

Chemistry A European J

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Electron delocalization of new mixed-valent (MV) systems with the aid of lateral metal chelation is reported. 2,2'-Bipyridine (bpy) derivatives with one or two appended di-p-anisylamino groups on the 5,5'-positions and a coordinated [Ru(bpy)(2)] (bpy = 2,2'-bipyridine), [Re(CO)(3)Cl], or [Ir(ppy)(2)] (ppy = 2-phenylpyridine) component were prepared. The single-crystal molecular structure of the bis-amine ligand without metal chelation is presented. The electronic properties of these complexes were studied and compared by electrochemical and spectroscopic techniques and DFT/TDDFT calculations. Compounds with two di-p-anisylamino groups were oxidized by a chemical or electrochemical method and monitored by near-infrared (NIR) absorption spectral changes. Marcus-Hush analysis of the resulting intervalence charge-transfer transitions indicated that electron coupling of these mixed-valent systems is enhanced by metal chelation and that the iridium complex has the largest coupling. TDDFT calculations were employed to interpret the NIR transitions of these MV systems.

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Section: Resultsmentioning

confidence: 99%

Electronic Coupling between Two Amine Redox Sites through the 5,5′‐Positions of Metal‐Chelating 2,2′‐Bipyridines

Nie

Chen

Yao

et al. 2012

Chemistry A European J

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“…It is known that the basicity of triarylamines is too low to interact with protons or metal ions. [23] Shown in Figure 2 are the normalized fluorescence spectra of 2 in hexane, THF, acetonitrile, and methanol. ABDI 2 OM is essentially nonfluorescent in acetonitrile and the three protic solvents.…”

Section: Electronic Spectramentioning

confidence: 99%

The N‐Arylamino Conjugation Effect in the Photochemistry of Fluorescent Protein Chromophores and Aminostilbenes

Huang¹,

Yang²

2010

Chemistry An Asian Journal

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To understand the nonradiative decay mechanism of fluorescent protein chromophores in solutions, a systematic comparison of a series of (Z)-4-(N-arylamino)benzylidene-2,3-imidazolinones (ABDIs: 2 P, 2 PP, 2 OM, and 2 OMB) and the corresponding trans-4-(N-arylamino)-4'-cyanostilbenes (ACSs: 1 P, 1 PP, 1 OM, and 1 OMB) was performed. We have previously shown that the parameter Phi(f)+2 Phi(tc), in which Phi(f) and Phi(tc) are the quantum yields of fluorescence and trans-->cis photoisomerization, respectively, is an effective probe for evaluating the contribution of twisted intramolecular charge transfer (TICT) states in the excited decays of trans-aminostilbenes, including the push-pull ACSs. One of the criteria for postulating the presence of a TICT state is Phi(f)+2 Phi(tc)<<1.0, because its formation is decoupled with the C=C bond (tau) torsion pathway and its decay is generally nonradiative. Our results show that the same concept also applies to ABDIs 2 with the parameter Phi(f)+2 Phi(ZE) in which Phi(ZE) is the quantum yield of Z-->E photoisomerization. We conclude that the tau torsion rather than the C-C bond (phi) torsion is responsible for the nonradiative decays of ABDIs 2 in aprotic solvents (hexane, THF, acetonitrile). The phenyl-arylamino C--N bond (omega) torsion that leads to a nonradiative TICT state is important only for 2 OM in THF and acetonitrile. If the solvent is protic (methanol and 10-20 % H(2)O in THF), a new nonradiative decay channel is present for ABDIs 2, but not for ACSs 1. It is attributed to internal conversion (IC) induced by solvent (donor)-solute (acceptor) hydrogen-bonding (HB) interactions. The possible HB modes and the concept of tau torsion-coupled proton transfer are also discussed.

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“…Trans-aminostilbenes are a class of p-donor-acceptor (D-A) systems that have been investigated as fluorescent probes [1][2][3][4][5][6], cell imaging dyes [7][8][9], and the active materials in a variety of optoelectronic devices such as organic light-emitting diodes [10,11], dye-sensitized solar cells [12][13][14], nonlinear optics [15][16][17][18][19][20], and molecular switches [21,22]. These applications are all associated with the electronically excited states, in which the lowest singlet excited state (S 1 ) possesses a significant degree of charge separation as a result of intramolecular charge-transfer (ICT) from the amino to the stilbene moiety upon photoexcitation.…”

Section: Introductionmentioning

confidence: 99%

Fate of photoexcited trans-aminostilbenes

Yang

Lin

2015

Journal of Photochemistry and Photobiology A: Chemistry

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Palladium-Catalyzed Synthesis of trans-4-(N,N-Bis(2-pyridyl)amino)stilbene. A New Intrinsic Fluoroionophore for Transition Metal Ions

Cited by 48 publications

References 20 publications

Electronic Coupling between Two Amine Redox Sites through the 5,5′‐Positions of Metal‐Chelating 2,2′‐Bipyridines

Electronic Coupling between Two Amine Redox Sites through the 5,5′‐Positions of Metal‐Chelating 2,2′‐Bipyridines

The N‐Arylamino Conjugation Effect in the Photochemistry of Fluorescent Protein Chromophores and Aminostilbenes

Fate of photoexcited trans-aminostilbenes

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