Photoinduced Intramolecular Charge Separation in Donor/Acceptor-Substituted Bicyclohexylidene and Bicyclohexyl

Hoogesteger, Frans J.; Walree, Cornelis A. van; Jenneskens, Leonardus W.; Roest, Martin R.; Verhoeven, J. W.; Schuddeboom, Wouter; Piet, Jacob J.; Warman, John M.

doi:10.1002/1521-3765(20000818)6:16<2948::aid-chem2948>3.0.co;2-0

Cited by 31 publications

(9 citation statements)

References 22 publications

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“…Transport has been related to a favorable intramolecular interaction between the sulfur functionalities and the olefinic p orbitals, which are mediated by the s C-C orbital system (throughbond interactions). Photo-electron spectroscopy 22 and photo-induced-electron transfer experiments 23,24 have confirmed the occurrence of transannular electronic interactions mediated via the s-p-s hydrocarbon skeleton. Fig.…”

Section: Molecular Junctions With Oligo(cyclohexylidene)mentioning

confidence: 74%

Molecular three-terminal devices: fabrication and measurements

et al. 2006

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Incorporation of a third, gate electrode in the device geometry of molecular junctions is necessary to identify the transport mechanism. At present, the most popular technique to fabricate three-terminal molecular devices makes use of electromigration. Although it is a statistical process, we show that control over the gap resistance can be obtained. A detailed analysis of the current-voltage characteristics of gaps without molecules, however, shows that they reveal features that can mistakenly be attributed to molecular transport. This observation raises questions about which gaps with molecules can be disregarded and which not. We show that electrical characteristics can be controlled by the rational design of the molecular bridge and that vibrational modes probed by electrical transport are of potential interest as molecular fingerprints.

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Section: Molecular Junctions With Oligo(cyclohexylidene)mentioning

confidence: 74%

Molecular three-terminal devices: fabrication and measurements

et al. 2006

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“…An additional attractive aspect, especially of tetrahydro-4H-thiopyran end-capped oligo(cyclohexylidenes), is that they exhibit an alternating σ-π orbital topology, which enables them to relay electronic interactions via a through-bond orbital mechanism. [23][24][25] Hence, various functionalized oligo-(cyclohexylidenes) have already found application in molecular electronics and as active spacers in devices. [25][26][27][28] Procedures for SAM formation of tetrahydro-4H-thiopyran end-functionalized oligo(cyclohexylidenes) were previously reported.…”

Section: Introductionmentioning

confidence: 97%

“…[23][24][25] Hence, various functionalized oligo-(cyclohexylidenes) have already found application in molecular electronics and as active spacers in devices. [25][26][27][28] Procedures for SAM formation of tetrahydro-4H-thiopyran end-functionalized oligo(cyclohexylidenes) were previously reported. 25,29,30 It was shown that they form well-ordered SAMs, even when they consist of a single cyclohexane-type ring.…”

Section: Introductionmentioning

confidence: 99%

“…[25][26][27][28] Procedures for SAM formation of tetrahydro-4H-thiopyran end-functionalized oligo(cyclohexylidenes) were previously reported. 25,29,30 It was shown that they form well-ordered SAMs, even when they consist of a single cyclohexane-type ring. Apparently, during SAM formation, the sulfide moiety (tetrahydro-4H-thiopyran unit) of our end-functionalized oligo(cyclohexylidenes) interacts with the Au(111) surface through a dative bond by physisorption.…”

Section: Introductionmentioning

confidence: 99%

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Mixed Self-Assembled Monolayers of Semirigid Tetrahydro-4H-thiopyran End-Capped Oligo(cyclohexylidenes)

et al. 2005

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Single-component and mixed self-assembled monolayers (SAMs) of one-and three-ring semirigid tetrahydro-4H-thiopyran end-capped oligo(cyclohexylidenes)sthat is, thiopyran (1), 4-(4-cyclohexylidenecyclohexylidene)tetrahydro-4H-thiopyran (2), and 4-(tetrahydro-4H-thiopyran-4-cyclohexylidene-4′-ylidene)-tetrahydro-4H-thiopyran (3)son Au(111) substrates have been prepared and studied by cyclic voltammetry (CV), atomic force microscopy (AFM), and scanning tunneling microscopy (STM). It was found that the shortest adsorbate 1 more readily forms a SAM than 2 or 3. Notwithstanding, the SAMs of 2 or 3 are thermodynamically more stable due to favorable intermolecular attractions. Holes were made with the AFM tip establishing tilt angles of 30-50°with respect to the surface normal for all SAMs. STM imaging showed well-ordered, line-shaped packing patterns with molecular resolution for the SAM of 2. Similar patterned structures were not observed for 1 and 3. Mixed SAMs were prepared by exposing a SAM of 1 to ethanol solutions of either 2 or 3. STM imaging revealed that domains of molecules of 2 or 3 amidst a monolayer of 1 are formed in both cases. Whereas in the mixed SAM of 1 and 2 the domains are irregularly shaped, circular islands of uniform size are found in the mixed SAM of 1 and 3.

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“…The electron donor is an N,Ndialkylanilino moiety and the electron acceptor is a 1,1-dicyanovinyl group. Photoinduced charge separation and recombination processes in a variety of compounds containing this donor-acceptor combination and a -or ---bridge have been extensively investigated by us [13][14][15] and others. 16 For model compound 3 it was shown by the presence of a weak intramolecular CT absorption band that the four--bond bridge relays a weak through-bond interaction between the donor and acceptor.…”

Section: Introductionmentioning

confidence: 99%

Charge transfer interactions in polyesters with a donor‐(σ‐bridge)‐acceptor moiety in the repeating unit

Oosterbaan

Kaats-Richters

Jenneskens

et al. 2004

J. Polym. Sci. A Polym. Chem.

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Two high molecular weight linear polyesters were investigated to gain insight in how the photophysics of electron donor-(-spacer)-electron acceptor (DA) compounds are affected by incorporation into a polymer. They were prepared by condensation of either adipoyl or sebacoyl chloride with a diol that was functionalized with an N,N-dialkylaniline donor, a cyclohexyl type -spacer, and a 1,1-dicyanovinyl acceptor. The solubility, which is very low, and the thermal properties of the polyesters are dictated by physical crosslinking as a consequence of interchain donor-acceptor interactions. Charge transfer (CT) absorption and emission are observed, which involve CT between DA moieties of different chains rather than CT processes within a single DA unit. As a result, the photophysics of the DA units in the polyesters differs strongly from that of similar DA compounds in solution. Upon swelling the polymers with THF, the CT fluorescence disappears partly. Analogous polymers containing only an N,N-dialkylaniline donor display dual fluorescence; one band reflects local emission, while the other is attributed to excimer emission.

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Photoinduced Intramolecular Charge Separation in Donor/Acceptor-Substituted Bicyclohexylidene and Bicyclohexyl

Cited by 31 publications

References 22 publications

Molecular three-terminal devices: fabrication and measurements

Molecular three-terminal devices: fabrication and measurements

Mixed Self-Assembled Monolayers of Semirigid Tetrahydro-4H-thiopyran End-Capped Oligo(cyclohexylidenes)

Charge transfer interactions in polyesters with a donor‐(σ‐bridge)‐acceptor moiety in the repeating unit

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