Bridged Triphenylamine-Based Dendrimers: Tuning Enhanced Two-Photon Absorption Performance with Locked Molecular Planarity

Fang, Zhen; Teo, Tang-Lin; Cai, Liping; Lai, Yongqing; Samoc̀, Anna; Samoć, Marek

doi:10.1021/ol801238n

Cited by 101 publications

(100 citation statements)

References 47 publications

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“…The angle between the two methyl groups is 1088,s imilar to that obtained from X-ray structure analysis for similar triarylamines. [20] Additionally,o n Cu(111)a no ut-of-surface displacemento ft he Cu atom underneath the Na tom of the cyano group of approximately 0.2 i s observed, but neither the Ag nor the Au surface undergoes any noticeable restructuring. The stronger N-Cu interaction is also manifested in stronger overlapo ft he van derW aals radii of the Na nd Cu atoms [35] compared to 1 on Ag(111)o rA u(111) ( Table 2).…”

Section: Computational Resultsmentioning

confidence: 93%

“…The synthesis of 2,6,10-tribromo-4,4,8,8,12,12-hexamethyl-4H,8H,12H-benzo[1,9]qui-nolizino[3,4,5,6,7-defg]acridine (2)w as performed according to the literature procedure. [20] Melting points were determined in open capillaries with aB üchi M-560 melting-point apparatus. Sample preparation and measurements:A ll experiments were performed under ultrahigh vacuum (UHV).…”

Section: Experimental and Theoretical Details Experimental Detailsmentioning

confidence: 99%

“…Such planarized triarylamines, so-called heterotriangulenes, are at presento fg rowing interest owing to their potential as stable electron-rich building blocksf or optoelectronic organic materials. [19,20] In our recent study on the self-assembly of 1 on Au(111), we could show that the molecules can undergo H-bonding, dipolar coupling and metal-ligandi nteraction. [21] By comparing these results to the self-assembly on Ag(111)a nd Cu(111), we aim to provide insighti nto the subtle interplay between molecule-substrate and intermolecular interactions leading to significant differences in the selfassembled patterns.…”

Section: Introductionmentioning

confidence: 98%

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Cyano‐Functionalized Triarylamines on Coinage Metal Surfaces: Interplay of Intermolecular and Molecule–Substrate Interactions

Müller

Moreno-López

Gottardi

et al. 2015

Chemistry A European J

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The self-assembly of cyano-functionalized triarylamine derivatives on Cu(111), Ag(111) and Au(111) was studied by means of scanning tunnelling microscopy, low-energy electron diffraction, X-ray photoelectron spectroscopy and density functional theory calculations. Different bonding motifs, such as antiparallel dipolar coupling, hydrogen bonding and metal coordination, were observed. Whereas on Ag(111) only one hexagonally close-packed pattern stabilized by hydrogen bonding is observed, on Au(111) two different partially porous phases are present at submonolayer coverage, stabilized by dipolar coupling, hydrogen bonding and metal coordination. In contrast to the self-assembly on Ag(111) and Au(111), for which large islands are formed, on Cu(111), only small patches of hexagonally close-packed networks stabilized by metal coordination and areas of disordered molecules are found. The significant variety in the molecular self-assembly of the cyano-functionalized triarylamine derivatives on these coinage metal surfaces is explained by differences in molecular mobility and the subtle interplay between intermolecular and molecule-substrate interactions.

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Section: Computational Resultsmentioning

confidence: 93%

Section: Experimental and Theoretical Details Experimental Detailsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

See 1 more Smart Citation

Cyano‐Functionalized Triarylamines on Coinage Metal Surfaces: Interplay of Intermolecular and Molecule–Substrate Interactions

Müller

Moreno-López

Gottardi

et al. 2015

Chemistry A European J

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“…The CTPA compounds 1 , 2 and 3 were synthesized from known O,O',O'' -amino-trisbenzoic acid-trimethylester ( S1 )62, upon halogenation with I 2 in the presence Ag 2 SO 4 and N -bromosuccinimide, respectively, followed by saponification and Lewis acid-catalysed Friedel–Crafts acylation of the in situ formed acid chloride. For experimental details and characterization data, see Supplementary Methods and Supplementary Fig.…”

Section: Methodsmentioning

confidence: 99%

Hierarchical on-surface synthesis and electronic structure of carbonyl-functionalized one- and two-dimensional covalent nanoarchitectures

et al. 2017

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The fabrication of nanostructures in a bottom-up approach from specific molecular precursors offers the opportunity to create tailored materials for applications in nanoelectronics. However, the formation of defect-free two-dimensional (2D) covalent networks remains a challenge, which makes it difficult to unveil their electronic structure. Here we report on the hierarchical on-surface synthesis of nearly defect-free 2D covalent architectures with carbonyl-functionalized pores on Au(111), which is investigated by low-temperature scanning tunnelling microscopy in combination with density functional theory calculations. The carbonyl-bridged triphenylamine precursors form six-membered macrocycles and one-dimensional (1D) chains as intermediates in an Ullmann-type coupling reaction that are subsequently interlinked to 2D networks. The electronic band gap is narrowed when going from the monomer to 1D and 2D surface-confined π-conjugated organic polymers comprising the same building block. The significant drop of the electronic gap from the monomer to the polymer confirms an efficient conjugation along the triphenylamine units within the nanostructures.

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“…1 Synthesis of DTPA (11b). Synthesized according to general procedure E using tris-(4-((E)-4-bromostyryl)phenyl)amine 10 (0.3 g, 0.038 mmol) and 1,3-bis(dodecyloxy)-5-vinylbenzene 5b 13 …”

Section: Tris-(4-((e)-4-bromostyryl)phenyl)amine (10) 31mentioning

confidence: 99%

Synthesis and photophysical properties of triphenylamine-based multiply conjugated star-like molecules

et al. 2015

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Novel triphenylamine-based star-like molecules 11 were synthesized and characterized using FT-IR, 1 H, 13 C, and DEPT-135 NMR spectroscopy, and MALDI-TOF mass spectrometry. The absorption and emission spectra of star-like molecules were studied in different solvents. The effect of solvent polarity and aggregation studies on the absorption and emission spectra has also been studied. The new starlike molecules are found to exhibit broad absorption and emission band along with intramolecular charge transfer character. The fluorescence spectra of triphenylamine derivatives shift from blue to green wavelength on increasing the extended conjugation of the molecule. The experimental results indicate that there is cooperative enhancement originating from the inter-branch coupling and an increase in the light-harvesting ability upon increasing the conjugated molecule size.

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Bridged Triphenylamine-Based Dendrimers: Tuning Enhanced Two-Photon Absorption Performance with Locked Molecular Planarity

Cited by 101 publications

References 47 publications

Cyano‐Functionalized Triarylamines on Coinage Metal Surfaces: Interplay of Intermolecular and Molecule–Substrate Interactions

Cyano‐Functionalized Triarylamines on Coinage Metal Surfaces: Interplay of Intermolecular and Molecule–Substrate Interactions

Hierarchical on-surface synthesis and electronic structure of carbonyl-functionalized one- and two-dimensional covalent nanoarchitectures

Synthesis and photophysical properties of triphenylamine-based multiply conjugated star-like molecules

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