Crystalline Thin Film of a Donor‐ Substituted Cyanoethynylethene for Nanoscale Data Recording Through Intermolecular Charge‐Transfer Interactions

Jiang, Guiyuan; Michinobu, Tsuyoshi; Yuan, Wenfang; Feng, Min; Wen, Yongqiang; Du, Shixuan; Gao, Hongjun; Jiang, Lei; Song, Yanlin; Diederich, François; Zhu, Daoben

doi:10.1002/adma.200500559

Cited by 55 publications

(23 citation statements)

References 39 publications

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“…Most of the known D‐π‐A chromophores feature a planar molecular scaffold to ensure efficient π‐conjugation between the donor and the acceptor moieties 2–10. These planar chromophores tend to form crystalline films by virtue of strong π–π stacking interactions and antiparallel molecular dipole alignment in the solid state 11. Their employment in optoelectronic devices, however, requires the formation of amorphous thin films which can achieve high homogeneity and optical quality over large areas 12.…”

Section: Introductionmentioning

confidence: 99%

“…[2][3][4][5][6][7][8][9][10] These planar chromophores tend to form crystalline films by virtue of strong p-p stacking interactions and antiparallel molecular dipole alignment in the solid state. [11] Their employment in optoelectronic devices, however, requires the formation of amorphous thin films which can achieve high homogeneity and optical quality over large areas. [12] Thus, the design of suitable nonplanar chromophores [13] that avoid the formation of crystalline films, is of upmost importance for their practical applications.…”

Section: Introductionmentioning

confidence: 99%

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Donor–Acceptor (D–A)‐Substituted Polyyne Chromophores: Modulation of Their Optoelectronic Properties by Varying the Length of the Acetylene Spacer

Štefko

Tzirakis

Breiten

et al. 2013

Chemistry A European J

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A series of donor-acceptor-substituted alkynes, 2 a-f, was synthesized in which the length of the π-conjugated polyyne spacer between the N,N-diisopropylanilino donor and the 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) acceptor was systematically changed. The effect of this structural change on the optoelectronic properties of the molecules and, ultimately, their third-order optical nonlinearity was comprehensively investigated. The branched N,N-diisopropyl groups on the anilino donor moieties combined with the nonplanar geometry of 2 a-f imparted exceptionally high solubility to these chromophores. This important property allowed for performing INADEQUATE NMR measurements without (13) C labeling, which, in turn, resulted in a complete assignment of the carbon skeleton in chromophores 2 a-f and the determination of the (13) C-(13) C coupling constants. This body of data provided unprecedented insight into characteristic (13) C chemical shift patterns in push-pull-substituted polyynes. Electrochemical and UV/Vis spectroscopic studies showed that the HOMO-LUMO energy gap decreases with increasing length of the polyyne spacer, while this effect levels off for spacers with more than four acetylene units. The third-order optical nonlinearity of this series of molecules was determined by measuring the rotational averages of the third-order polarizabilities (γrot ) by degenerate four-wave mixing (DFWM). These latter studies revealed high third-order optical nonlinearities for the new chromophores; most importantly, they provided fundamental insight into the effect of the conjugated spacer length in D-A polyynes, that can be exploited in the future design of suitable charge-transfer chromophores for applications in optoelectronic devices.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Donor–Acceptor (D–A)‐Substituted Polyyne Chromophores: Modulation of Their Optoelectronic Properties by Varying the Length of the Acetylene Spacer

Štefko

Tzirakis

Breiten

et al. 2013

Chemistry A European J

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“…In collaborating with Diederich et al, [18] we prepared high-quality crystalline thin films based on the self assembly of 1,1,2-tricyano-2-[(4-dimethylaminophenyl)ethynyl]ethene (TDMEE) (Scheme 2) molecules using the vacuum-deposition method. The molecules undergo p-stacking in the crystalline thin films, and the packing adopts regular alternate donor/acceptor stacks.…”

Section: G Jiang Et Al / Organic Functional Moleculesmentioning

confidence: 99%

Organic Functional Molecules towards Information Processing and High‐Density Information Storage

et al. 2008

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In this Progress Report, we discuss our recent achievements in design and synthesis of new functional molecules towards information processing at the molecular level and high‐density information storage. These include: 1) new molecular switches, logic gates, and combinational logic circuits based on molecules and ensembles with photochromic spiropyran units that undergo reversible structural transformation among multistates, in response to external inputs such as light, protons, and metal ions; 2) high‐density information storage, mainly focusing on nanometer‐scale electrical recording based on the conductance transition of organic molecules, and multimode data storage on multiresponsive molecules. Relevant progress and an outlook in this area are also discussed.

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“…A high-quality crystalline thin film (ca. 20 nm thickness) of donor-substituted CEE 17a was vacuum-deposited on highly oriented pyrolytic graphite (HOPG) [80]. In this film, molecules of 17a stack with a favorable antiparallel molecular dipole orientation and an interchromophoric distance of 3.44 Å.…”

Section: Cyanoethynylethenes: Property Tuning In Charge-transfer Chromentioning

confidence: 99%

Conjugation and optoelectronic properties of acetylenic scaffolds and charge-transfer chromophores

Kivala

Diederich

2008

Pure and Applied Chemistry

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Our group started a research program in acetylene chemistry in 1987; since then, an intense research effort led to a fascinating journey into acetylenic scaffolding, aimed at exploring conjugative and optoelectronic properties of acetylenic chromophores. This journey included the generation of a unique molecular construction kit for acetylenic scaffolding, consisting of (E)-1,2-diethynylethenes [DEEs, (E)-hex-3-ene-1,5-diynes], tetraethynylethenes (TEEs, 3,4-diethynylhex-3-ene-1,5-diynes), chiral 1,3-diethynylallenes (DEAs, hepta-3,4-diene-1,6-diynes), 1,4-di and 1,1,4,4-tetraethynylbutatrienes, chiral trialkynylmethanes, and 1,1,2,2-tetraethynylethanes. These building modules were subsequently applied to the synthesis of carbon-rich architectures extending into one, two, and three dimensions. They include multinanometer-long monodisperse oligomers as models for infinite acetylenic polymers, molecular switches, perethynylated dehydroannulenes, expanded radialenes, and radiaannulenes, and an octamethoxy-substituted expanded cubane with a central C 56 core. Donor-substituted cyanoethynylethenes (CEEs) and 1,1,4,4-tetracyanobuta-1,3-dienes (TCBDs) were introduced as new push-pull chromophores featuring intense intramolecular charge-transfer (CT) interactions. Dendritic multivalent CT chromophores were constructed using atom-economic, "click"-like reactions, and these systems were shown to behave as "molecular batteries", featuring exceptional electron uptake and storage capacity. The research finally led to the development of an unprecedented cascade reaction for the preparation of dendritic and oligomeric donor-acceptor (D-A) molecules. New [AB]-type oligomers become accessible in domino reactions involving repetitive sequences of [2+2] cycloadditions of tetracyanoethylene (TCNE) and tetrathiafulvalene (TTF) to polyynes, followed by retro-electrocyclizations.

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Crystalline Thin Film of a Donor‐ Substituted Cyanoethynylethene for Nanoscale Data Recording Through Intermolecular Charge‐Transfer Interactions

Cited by 55 publications

References 39 publications

Donor–Acceptor (D–A)‐Substituted Polyyne Chromophores: Modulation of Their Optoelectronic Properties by Varying the Length of the Acetylene Spacer

Donor–Acceptor (D–A)‐Substituted Polyyne Chromophores: Modulation of Their Optoelectronic Properties by Varying the Length of the Acetylene Spacer

Organic Functional Molecules towards Information Processing and High‐Density Information Storage

Conjugation and optoelectronic properties of acetylenic scaffolds and charge-transfer chromophores

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