Donor‐Substituted 1,1,4,4‐Tetracyanobutadienes (TCBDs): New Chromophores with Efficient Intramolecular Charge‐Transfer Interactions by Atom‐Economic Synthesis.

Michinobu, Tsuyoshi; Boudon, Corinne; Gisselbrecht, Jean‐Paul; Seiler, Paul; Frank, Brigitta; Moonen, Nicolle N. P.; Gross, Maurice; Diederich, François

doi:10.1002/chin.200625095

Cited by 19 publications

(39 citation statements)

References 1 publication

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“…The key reagent of this project is cyano-containing strong acceptor molecules, which are originally p-type doping reagents, but undergo [2?2] cycloaddition with electrondonor-activated alkynes [21,22]. The cyclobutene intermediates formed by the [2?2] cycloaddition are smoothly transformed into donor-acceptor type products via ring opening.…”

Section: Introductionmentioning

confidence: 99%

Postfunctionalization of aromatic polyamine by [2+2] cycloaddition of 7,7,8,8-tetracyanoquinodimethane with side chain alkynes

Murata

Michinobu

2011

Polym. Bull.

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Electron-rich, side chain alkynes of an aromatic polyamine were functionalized by a [2?2] cycloaddition, followed by retro-cyclization with the electronaccepting 7,7,8,8-tetracyanoquinodimethane (TCNQ). 1 H NMR studies were used to optimize the reaction conditions. Mild heating to [50°C afforded the postfunctionalized aromatic polyamines with the desired acceptor amounts. The quantitative TCNQ addition was demonstrated by the MALDI-TOF mass spectrum and elemental analysis. Introduction of the cyano-based acceptor moieties into the polymer side chains resulted in unusually strong intermolecular interactions. In addition to the p-p interactions of the extended acceptor moieties, these intermolecular forces were supposed to improve the thermal stability of the aromatic polymers. Furthermore, the donor-acceptor chromophores formed by this postfunctionalization displayed low energy charge-transfer bands and redox activities in both the anodic and cathodic directions. The straightforward postfunctionalization technique using the alkyne-TCNQ addition is useful for the preparation of narrow band gap polymers in one step.

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Section: Introductionmentioning

confidence: 99%

Postfunctionalization of aromatic polyamine by [2+2] cycloaddition of 7,7,8,8-tetracyanoquinodimethane with side chain alkynes

Murata

Michinobu

2011

Polym. Bull.

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“…This compound was designed for organic transistor applications but its electron-rich nature is perfectly suited to electron-poor adducts such as nitriles and formed the basis for the work on the novel panchromatic chromophore investigated in this study. Following the extensive work by Diederich (Michinobu et al, 2006) and Shoji (Shoji et al, 2008;Shoji et al, 2009;Shoji et al, 2011) on single and double alkyne cycloadditions with nitrile adducts via a ring-opening of tetracyanocyclobutene intermediates, 7,7,8,8-tetracyanoquinodimethane (TCNQ) was added in a similar fashion to the electron-rich molecular rod and afford the target material in moderate yield (45 %). The synthetic route was designed to include hexyl chains to ensure solubility of all intermediates in common organic solvents and processability of the final target LB154.…”

Section: Resultsmentioning

confidence: 99%

A bifunctional smart material: the synthesis of a metal-free black pigment for optoelectronic applications from an organic semiconducting molecular rod

Jones

Luo

Kazlauciunas

et al. 2018

PRT

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A bifunctional smart material: the synthesis of a metal-free black pigment for optoelectronic applications from an organic semiconducting molecular rod. Pigment and Resin Technology, 47 (1). AbstractPurpose -To synthesise and evaluate the properties of a novel smart material consisting of a metal-free organic black pigment with a unique chromophore for bifunctional applications in optoelectronics.Design/methodology/approach -A robust and highly efficient organic reaction, namely, a double [2 + 2] cycloaddition, was deployed to transform a rod-like structure for chargetransfer applications to a strongly-conjugated light-absorbing molecule for both optical and electronic applications.Findings -The synthesis and characterisation of an air-stable metal-free black pigment is reported which contains an unconventional donor-acceptor panchromatic chromophore with an absorption window spanning 600 nm; the compound was synthetically converted from an organic semiconducting molecular rod and retains strong charge-transfer properties. The chromophore is comprised of tetracyanoquinodimethane (TCNQ) adduct either side of a dithienothiophenyl (DTT) core, capped with hexyl thiophenes that ensures solubility in common organic solvents. Its propensity to form excellent thin-films on different substrates such as glass and paper, with a total opacity in organic solvent, gives it the potential for wideranging applications in organic optoelectronics. Research limitations/implications -The synthetic chemistry and fundamental propertiesare investigated in the present study, with more detailed treatments and analysis to be soon developed. One leading smart material is presented, with further derivatives under investigation.Practical implications -The work presented shows the possibility of converting structures from one application to another with relative ease, but retain properties for both, using wellknown and facile conditions. Originality / value -The structures are novel, and an enhanced air-stable organic panchromatic chromophore is reported for processing in common organic solvents.

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“…For T-1 and R-1 here, the hydrophobic tetraphenyl unit and long alkyl chain in one end of the molecule favor the non-polar CHCl 3 . On the contrary, the other end with the TCBD moiety is polar because of the intramolecular chargetransfer [80], which prefers the polar solvent MeOH to CHCl 3 . In the combined solvent system here, T-1 and R-1 become amphiphilic molecules that might assemble into layered structures and finally close to form vesicles.…”

Section: Shuttling Movement For Controlling Nanostructural Morphologiesmentioning

confidence: 99%

Self-assembly of Functional Molecular Shuttles Based on Organic Conjugated Molecules

Liu²,

2011

COC

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The aim of this article is to explore the molecular design, synthesis and construction of molecular shuttles based on conjugated organic molecules with photo-electronic activity by self-assembly techniques. The new functions of molecular shuttles, such as switching surface properties, protecting dyes and insulating molecular wires, controlling the energy transfer, controlling nanostructural morphologies, molecular transporting and multilevel fluorescence switching, are also discussed.

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Donor‐Substituted 1,1,4,4‐Tetracyanobutadienes (TCBDs): New Chromophores with Efficient Intramolecular Charge‐Transfer Interactions by Atom‐Economic Synthesis.

Cited by 19 publications

References 1 publication

Postfunctionalization of aromatic polyamine by [2+2] cycloaddition of 7,7,8,8-tetracyanoquinodimethane with side chain alkynes

Postfunctionalization of aromatic polyamine by [2+2] cycloaddition of 7,7,8,8-tetracyanoquinodimethane with side chain alkynes

A bifunctional smart material: the synthesis of a metal-free black pigment for optoelectronic applications from an organic semiconducting molecular rod

Self-assembly of Functional Molecular Shuttles Based on Organic Conjugated Molecules

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