Oligomers and Polymers Based on Pentacene Building Blocks

Lehnherr, Dan; Tykwinski, Rik R.

doi:10.3390/ma3042772

Cited by 27 publications

(23 citation statements)

References 116 publications

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“…This significantly influences the stability of higher acenes and it is in agreement with experimentally known facts that higher acenes are instable and harder to synthetize when compared to pentacene [57]. Mentioned issues related to oxidation of pentacene results in problematic procession of pentacene, which finally consequences in the fact that thermal vapor deposition method should be used [53].…”

Section: Oxidation and Reduction Potentialssupporting

confidence: 75%

“…This drawback is due the fact that pentacene is easily oxidized in air, while poor solubility is a result of strong intermolecular forces due to the p-stacking [53]. Thus, it was interesting for us to investigate the RP/OP, which can be interpreted as the tendency of structure to gain/loose electrons and thus to become oxidized/reduced, of higher acenes and their BN analogues.…”

Section: Oxidation and Reduction Potentialsmentioning

confidence: 98%

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Optoelectronic properties of higher acenes, their BN analogue and substituted derivatives

Armaković

Holodkov

et al. 2016

Materials Chemistry and Physics

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Section: Oxidation and Reduction Potentialssupporting

confidence: 75%

Section: Oxidation and Reduction Potentialsmentioning

confidence: 98%

Optoelectronic properties of higher acenes, their BN analogue and substituted derivatives

Armaković

Holodkov

et al. 2016

Materials Chemistry and Physics

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“…Keywords: acenes · density functional calculations · donor-acceptor systems · matrix isolation · photochemistry enjoy considerable attention. [14,15] Three donor-acceptor substitution patterns involving the terminal positions are conceivable for pentacene. The 2,3-D 2 -9,10-A 2 (pattern A) and the 2,10-D 2 -3,9-A 2 (pattern B) arrangements of substituents allow for quinoid dipolar resonance structures involving the entire pentacene p system (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

The Influence of Terminal Push–Pull Substitution on the Electronic Structure and Optical Properties of Pentacenes

Tönshoff

Bettinger

2012

Chemistry A European J

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The synthesis of 2,3-R(2)-9,10-(OMe)(2)-substituted pentacenes (R=OMe, F, Br, CN; 1-4) from 2,3-R(2)-9,10-dimethoxy-6,13-dihydro-6,13-ethanopentacene-15,16-diones (α-diketone-bridged precursors) by photochemically induced bis-decarbonylation (Strating-Zwanenburg reaction) is described. Under matrix-isolation conditions (solid Ar, 10 K) the S(1) transitions of 1 and 2 undergo hypsochromic and those of 3 and 4 bathochromic shifts compared to parent pentacene. The S(1) transition wavelengths correlate well with the difference of substituent parameters σ(p). A computational analysis of the excited states at the CAM-B3LYP/6-311+G** level of theory provides an assignment of the electronic transitions. Photolysis in solution at room temperature yields red [R=OMe (1)], blue [R=Br (3), F (2)], and green [R=CN (4)] pentacenes. The compounds are oxygen-sensitive and have low solubility, but their formation can be monitored by UV/Vis and, in the case of R=CN, also by (1)H NMR spectroscopy. The S(1) transition in 4 does not show the typical pentacene fine structure in the electronic absorption spectrum. Photogeneration in the presence of oxygen leads to a number of photoproducts that could be identified by monitoring the reaction by (1)H NMR spectroscopy for R=OMe.

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“…However, reports of polymers containing pentacene or tetracene units are less common . The first ones were acene‐containing polyfluorenes 1 (Scheme ) active in OLEDs .…”

Section: Introductionmentioning

confidence: 99%

TIPS‐Tetracene‐ and TIPS‐Pentacene‐Annulated Poly(norbornadiene)s: Synthesis and Properties

Porz

Paulus

Höfle

et al. 2013

Macromol. Rapid Commun

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Front Cover: The properties of elastomers are exploited to trigger wrinkling instabilities in curved shells. Each electro-spun micro-or nanofi ber consists of a soft core and a stiff outer half-shell, which are length-mismatched because of differential solvent de-swelling. The fi bers only wrinkle after attaining a well-defi ned helical shape. A simple analytical model is proposed to fi nd the curvature and wrinkle wavelength. Further details can be found in the article by Stimulus-sensing biohybrid materials have attracted signifi cant interest as smart materials with applications especially in the biomedical fi eld. Such materials harnessing unique properties of chemical and biological polymers are engineered to translate molecular stimuli into precisely defi ned mechanical material properties. This article gives an overview of how biological polymers can be used to control material properties and on their applications.

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Oligomers and Polymers Based on Pentacene Building Blocks

Cited by 27 publications

References 116 publications

Optoelectronic properties of higher acenes, their BN analogue and substituted derivatives

Optoelectronic properties of higher acenes, their BN analogue and substituted derivatives

The Influence of Terminal Push–Pull Substitution on the Electronic Structure and Optical Properties of Pentacenes

TIPS‐Tetracene‐ and TIPS‐Pentacene‐Annulated Poly(norbornadiene)s: Synthesis and Properties

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