Extendable nickel complex tapes that reach NIR absorptions

Audi, Hassib; Chen, Zhongrui; Charaf-Eddin, Azzam; D’Aléo, Anthony; Canard, Gabriel; Jacquemin, Denis; Siri, Olivier

doi:10.1039/c4cc07353c

Cited by 29 publications

(37 citation statements)

References 31 publications

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“…Quinoidal precursors 2 (Bandrowski base) 41 and 3 42 were reacted with the aldehyde 4previously unknown -in EtOH in the presence of piperidine to afford the expected benzobis(imidazoles) 5 and 6, respectively, in 46 and 49 % yields (Scheme 1). In situ deprotection -using TBAF (tetra-n-butylammonium fluoride) -gave target compounds A and B, which could be readily reacted in the presence of gold either as molecular junction, or as unit able to form self-assembled monolayers, because of the presence of terminal -SH thiol functions.…”

Section: Synthesis Of the Molecular Switch A And B And Characterizatimentioning

confidence: 99%

Electrical molecular switch addressed by chemical stimuli

et al. 2020

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We demonstrate that the conductance switching of benzo-bis(imidazole) molecules upon protonation depends on the lateral functional groups. The protonated H-substituted molecule shows a higher conductance than the neutral one (Gpro>Gneu), while the opposite (Gneu>Gpro) is observed for a molecule laterally functionalized by amino-phenyl groups. These results are demonstrated at various scale lengths : self-assembled monolayer, tiny nanodot-molecule junction and single molecules. From ab-initio theoretical calculations, we conclude that for the H-substituted molecule, the result Gpro>Gneu is correctly explained by a reduction of the LUMO-HOMO gap, while for the amino-phenyl functionnalized molecule, the result Gneu>Gpro is consistent with a shift of HOMO, which reduces the density of states at the Fermi energy.

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Section: Synthesis Of the Molecular Switch A And B And Characterizatimentioning

confidence: 99%

Electrical molecular switch addressed by chemical stimuli

et al. 2020

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“…9- 18 We also highlighted that the unsubstituted parent 3 behaves differently from 1 in coordination chemistry owing to the absence of N-substituents that allows the formation of polynuclear complexes with controlled lengths. 19 These observations suggest the study of QDIs 2 that can be viewed as the hybrid form of 1 and 3.…”

Section: Introductionmentioning

confidence: 97%

Di- vs. tetra-substituted quinonediimines: a drastic effect on coordination chemistry

et al. 2017

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We describe the first isolation of N,N'-disubstituted benzoquinonediimines (QDIs) 2 which revealed drastically different properties compared to N,N',N'',N'''-tetrasubstituted QDIs 1 due to the absence of N-substituents in the "upper part" of the molecule. Three major differences could be highlighted thanks to the present joint experimental and theoretical investigation: (1) the metalation with different metal precursors revealed a specific behaviour in coordination chemistry giving access to novel complexes with unprecedented stoichiometry and remarkable absorption properties. More specifically, a new monoplatinum complex that is able to absorb light from the UV up to the NIR region because of its unique delocalization pathway across the metal centre was obtained; (2) this new class of di-substituted QDIs showed an exceptionally broad pK range (ΔpK∼ 8) that could be explained by the possible tuning of the basicity of each imine which is now attainable; (3) these quinones could be used as reagents in organic synthesis to form the previously unknown N,N',N'',N'''-tetrasubstituted QDIs with tuneable substituents (aryl vs. alkyl), previously unknown, as a new ligand for coordination chemistry.

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“…In this strategy,t he ligand design is crucial since maximizing the conjugation through coordination requires keeping the p-d systems as coplanar as possible.Previous studies reported that low-lying p*o rbitals of quinoidal ligands can mix extensively with the valence d-orbitals of am etal center, yielding complexes in which the electrons could be delocalized over both the metal and the ligand. [15][16][17] In this context, derivatives of 2,5-diamino-1,4-benzoquinonediimines (2HQDI) are particularly appealing because of their fascinating optical properties, [18,19] and remarkable ability to serve as ligand in coordination chemistry.U nlike the N-substituted systems (N-alkyl or N-aryl), [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] the coordination chemistry of the parent (i.e.u nsubstituted) molecule 2HQDI in solution has been poorly investigated probably due to its low solubility and specific reactivity that induced unwanted side-reactions. [35] Some of us showed that the absence of N-substituents (no steric hindrance) allows au nique behavior resulting from the stepwise formation of coplanar polynuclear complexes NiQDI with up to 3r epeat units (n 3) ( Figure 1a).…”

Section: Introductionmentioning

confidence: 99%

1D Coordination π–d Conjugated Polymers with Distinct Structures Defined by the Choice of the Transition Metal: Towards a New Class of Antiaromatic Macrocycles

et al. 2020

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Recently p-d conjugated coordination polymers have received alot of attention owing to their unique material properties,although synthesis of long and defect-free polymers remains challenging. Herein we introduce an ovel on-surface synthesis of coordination polymers with quinoidal ligands under ultra-high vacuum conditions,whiche nables formation of flexible coordination polymers with lengths up to hundreds of nanometers.M oreover,t his procedure allows the incorporation of different transition-metal atoms with four-ortwo-fold coordination. Remarkably,t he twofold coordination mode revealed the formation of wires constituted by (electronically) independent 12-membered antiaromatic macrocycles linked together through two CÀCs ingle bonds.

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Extendable nickel complex tapes that reach NIR absorptions

Abstract: Stepwise synthesis of linear nickel complex oligomer tapes with no need for solid-phase support has been achieved. The control of the length in flat arrays allows a fine-tuning of the absorption properties from the UV to the NIR region.

Cited by 29 publications

References 31 publications

Electrical molecular switch addressed by chemical stimuli

Electrical molecular switch addressed by chemical stimuli

Di- vs. tetra-substituted quinonediimines: a drastic effect on coordination chemistry

1D Coordination π–d Conjugated Polymers with Distinct Structures Defined by the Choice of the Transition Metal: Towards a New Class of Antiaromatic Macrocycles

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