Electron‐Deficient Acridone Derivatives as a New Functional Core Towards Low‐Bandgap Metallopolyynes

Chow, Wing Cheong; Zhou, Guoquan; Wong, Wai Yeung

doi:10.1002/macp.200700091

Cited by 22 publications

(17 citation statements)

References 52 publications

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“…Another series of low-bandgap polymers P49 and P50 with electron-deficient acridone units was also reported recently. 56 Polymer P50 has E g of 2.10 eV which is greatly lowered compared to that for P49 (2.60 eV). Tuning of E g is accomplished by modification of the acridone ring based on cyano substitution.…”

Section: Effect Of a Donor-acceptor Structural Motifmentioning

confidence: 83%

Luminescent organometallic poly(aryleneethynylene)s: functional properties towards implications in molecular optoelectronics

Wong

2007

Dalton Trans.

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209

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This article highlights recent progress in the development of rigid-rod metallopolyyne polymers of late transition metals which can exhibit easily tunable luminescent and electronic properties. Considerable focus is placed on the design strategies towards the tuning capability of phosphorescence emission color and optical bandgap of this class of luminescent metallopolymers, and the evaluation of their suitability as emitters in light-emitting applications, optical power limiters for sensor protection and semiconductors in organometallic photovoltaic cells. An effective approach based on structural modification of the spacer group can be devised to achieve the full-color phosphorescence emission spanning almost the whole visible spectrum and to tune the material properties of these functional organometallic polymers. The major advances, ongoing challenges and future perspectives of this research frontier are also discussed.

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Section: Effect Of a Donor-acceptor Structural Motifmentioning

confidence: 83%

Luminescent organometallic poly(aryleneethynylene)s: functional properties towards implications in molecular optoelectronics

Wong

2007

Dalton Trans.

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209

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“…[8] While much effort has been devoted to spacers (Ar) like anthracene, carbazole, fluorene, oligothiophene, etc for the tuning of the S 1 and T 1 states (and hence E g ) in polymetallaynes, [8,9] most of these conjugated platinum(II) polyynes are very often characterized by rather large E g , which compare unfavorably with those of their organic competitors comprising alternating electron donor and acceptor units. [6,7] It was not until recently that low-bandgap platinum(II) polyyne polymers with the electron-deficient thieno [3,4-b]pyrazine, [10] dicyanomethylenefluorene, [11] silole [12] thienyl-heteroaryl hybrids [4h-4j] or dicyanomethyleneacridone [13] were prepared using such a D-A concept. It is known that the addition of electron-withdrawing imine nitrogen to a conjugated polymer backbone generally enhances its electron-accepting properties.…”

Section: Introductionmentioning

confidence: 99%

Organometallic Polymer Light‐Emitting Diodes Derived from a Platinum(II) Polyyne Containing the Bithiazole Ring

Wong

Zhou

et al. 2008

Macro Chemistry & Physics

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The synthesis, thermal, and photoluminescence properties of novel platinum metallopolyynes of bithiazole derivatives trans‐[Pt(PR3)2‐C≡C‐Ar‐C≡C]n (Ar = 4,4′‐dibutyl‐2,2′‐bithiazole‐5,5′‐diyl P1; 4,4′‐dinonyl‐2,2′‐bithiazole‐5,5′‐diyl P2) and their molecular model complexes are described. The structural properties of the dinuclear model compound for P1 have been examined by X‐ray crystallography. In view of the electron‐donating and electron‐withdrawing nature of the thiazole rings in the main chain, a strong π‐conjugated system that features unique donor–acceptor interactions is created, which results in optical bandgaps of 2.40 eV. The optical gap of the polymer is notably reduced as compared to that for the more electron‐rich bithienyl analogue. Multi‐layer polymer light‐emitting diodes have been fabricated with the metallopolymer as the emitting layer, which give a green light color with the Commission Internationale de L'Eclairage (CIE) chromaticity coordinates of (0.26, 0.58) at 8 V.magnified image

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“…The collected product was then triturated with cold pentane to afford 4b as a viscous dark red oil (0.2545 g, 0.2166 mmol, 73% yield). 1 13 …”

Section: Synthesismentioning

confidence: 97%

“…H NMR (400 MHz, chloroform-d) d 8.55 (dd, J = 8.3, 1.4 Hz, 2H), 7.70 (td, J = 8.6, 7.1, 1.5 Hz, 2H), 7.47 (d, J = 8.4 Hz, 2H), 7.33 (td, J = 8.2, 7.1, 1.0 Hz, 2H), 4.30 (t, 2H), 1.96 (p, J = 16.0, 8.0 Hz, 2H), 1.54-1.49 (m, 2H), 1.49-1.40 (m, 2H), 1.39-1.22 (m, 10H), 0.89 (t, 3H) 13. C NMR (101 MHz, CDCl 3 ) d 156.41, 138.92, 133.63, 127.25, 121.97, 118.21, 117.70, 114.31, 68.24, 48.21, 32.01, 29.71, 29.64, 29.42, 29.39, 27.09, 26.97, 22.81, 14.25.…”

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confidence: 98%

Structure–property relationship of donor–acceptor acridones – an optical, electrochemical and computational study

Thériault

Radford

Parvez

et al. 2015

Phys. Chem. Chem. Phys.

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The synthesis of two neutral acridone derivatives was carried out to design media sensitive chromophores by taking advantage of intramolecular charge transfer (ICT) features. The molecules comprised two different donor-acceptor-donor triads, with absorption maxima at 425 nm and 520 nm, for the ketone and dicyanomethylene derivatives, respectively. The ketone variant exhibited fluorescence at room temperature, whereas the dicyanomethylene derivative was only emissive in frozen hexane. The ketone emission was highly solvatochromic, with Stokes shifts that ranged from 5000 cm(-1) to 10 000 cm(-1). Electrochemically, both compounds displayed similar oxidation potentials at approximately 0.35 V versus ferrocene/ferrocenium, which was anticipated since both systems employ the same ethynylaniline donor portion of the molecule, whereas only the 9-dicyanomethylene derivative showed a reduction peak at -1.5 V vs. Fc/Fc(+). Additional spectroelectro-chemical experiments supported a delocalized cationic charge on the ethynylaniline fragments during oxidation and that during electrochemical reduction the dicyanomethylene moieties show localized anionic charge. All of the experimental observations are finally compared to DFT, TDDFT and NICS(0) computations to gain insight into the transitions involved and deduce the role of the acridone core in stabilizing its oxidized and reduced forms.

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Electron‐Deficient Acridone Derivatives as a New Functional Core Towards Low‐Bandgap Metallopolyynes

Cited by 22 publications

References 52 publications

Luminescent organometallic poly(aryleneethynylene)s: functional properties towards implications in molecular optoelectronics

Luminescent organometallic poly(aryleneethynylene)s: functional properties towards implications in molecular optoelectronics

Organometallic Polymer Light‐Emitting Diodes Derived from a Platinum(II) Polyyne Containing the Bithiazole Ring

Structure–property relationship of donor–acceptor acridones – an optical, electrochemical and computational study

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