Hydrocarbon Oligomers

Geerts, Yves; and, G. Klärner; Müllen, Kläus

doi:10.1002/9783527603220.ch1

Cited by 15 publications

(4 citation statements)

References 228 publications

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“…As shown in Figure 1, we explore structure-property relationships in these materials by comparing the polymer photophysics with oligomers, from dimer to pentamer. [28][29][30][31][32][33] We have recently reported the synthesis of a soluble polypentacene and its derivatives on the basis of well-defined oligomers. 34 The polymer (PPc, M n = 16 kg mol À1 , ä = 2.1) is synthesized by a Suzuki step-growth polymerization of bifunctional monomers and is regiorandom, as shown in Figure 1.…”

Section: Resultsmentioning

confidence: 99%

Singlet Fission in Polypentacene

Sanders

Kumarasamy

Pun

et al. 2016

Chem

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Singlet fission (SF), the conversion of a singlet exciton into two triplet excitons, has the potential to enhance single-junction photovoltaic efficiencies. Many groups have recently reported SF in molecular dimers. Here, Campos and colleagues report SF in a pentacene polymer. They also examine a series of well-defined oligomers to understand the changes in photophysics moving from the constrained dimer system to the extended pentacene polymer.

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Section: Resultsmentioning

confidence: 99%

Singlet Fission in Polypentacene

Sanders

Kumarasamy

Pun

et al. 2016

Chem

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“…The olympicene molecule, a five-ringed polyaromatic hydrocarbon (PAH), was recently synthesized . PAHs have long been studied in astrophysics, and they are now used as molecular semiconductors . Olympicene is related to a class of PAHs known as acenes and two-dimensional acene sheets, which represent finite approximations to graphene .…”

Section: Introductionmentioning

confidence: 99%

Theoretical Prediction of the Structures and Energies of Olympicene and its Isomers

Valentine

Mazziotti

2013

J. Phys. Chem. A

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Pentacene, a linear five-ringed polyaromatic hydrocarbon, has recently been used as an organic semiconductor in field-effect transistors. The recently synthesized olympicene molecule, so named because of its resemblance to the olympic rings, is a more compact five-ringed structure. This paper offers the first theoretical study of the kinetic stability of olympicene and its isomers. We use the parametric two-electron reduced density matrix (2-RDM) method, which takes the 2-RDM as the basic variable in lieu of the traditional wave function in calculations [ Mazziotti , D. A. Phys. Rev. Lett. 2008 , 101 , 253002 ]. Our calculations demonstrate that olympicene's isomers may be separated into aromatic and diradical isomers, the latter of which require accurate treatment of strong electron correlation to detect multireference character. Albeit formally a single-reference method, the parametric 2-RDM captures the multireference correlation of the diradical isomers; relative to olympicene, the 2-RDM predicts five diradical isomers that are 16-22 kcal/mol lower in energy than those from coupled cluster with single and double excitations-a significant change that causes these isomers to be stable to dissociation by 2-20 kcal/mol. We characterize the transition states between olympicene's isomers, observe differences in aromaticity among the different isomers, and compare the electronic properties of olympicene to those of pentacene. The olympicene molecule has the potential to complement pentacene as an organic semiconductor.

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“…Tailor-made molecules with well defined functions may act as switches, wires, diodes or memory units. [1][2][3][4][5][6] Further ad-vanced systems consisting of combinations of such electronically active molecules are already envisaged and designed to perform more complex logical functions like AND or XOR gates. 7 Finally, the vision of electronic circuits based on modular combinations of single molecules arises.…”

Section: Introductionmentioning

confidence: 99%

Electron Transfer Through Bridging Molecular Structures

Mayor

Büschel

Fromm³

et al. 2002

Annals of the New York Academy of Sciences

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Pairs of reducible pentakis(thiophenyl)benzene subunits are linked by different molecular structures as model compounds for reducible molecular-wire-type synthons showing varying electron-transfer ability as a function of the bridging structures, consisting of either para-divinylbenzene, bis-hydrazone, or diacetylene. Their electron-transfer ability from one reducible subunit to the other was investigated by electrochemical and spectroelectrochemical methods. In the case of the bis-hydrazone bridge and the diacetylene bridge, the solid-state structures support the experimental findings. While the para-divinylbenzene bridge completely isolates the reducible subunits (class I system) the diacetylene bridge electronically connects the two reducible structures (class III system), demonstrating its potential application as a "molecular wire." The bis-hydrazone linked dimer displays electronic communication only to a small extend, which was only observed in the spectroelectrochemical investigation. The diacetylene connection as active electron-transfer linker together with poly(thiophenyl)benzene as reducible subunits was used to design more complex molecular architectures. Linear rodlike struktures did allow adjustment of the length of these type of molecular wires and investigation of the extent of electron mobility. Cyclic structures addressed the possibility of moving electrons on a bent molecular wire.

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Hydrocarbon Oligomers

Cited by 15 publications

References 228 publications

Singlet Fission in Polypentacene

Singlet Fission in Polypentacene

Theoretical Prediction of the Structures and Energies of Olympicene and its Isomers

Electron Transfer Through Bridging Molecular Structures

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