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Search indexed NASA NTRS and DOE OSTI research on propulsion, heat transfer, battery materials and energy systems. Follow report and document links to the original sources.

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At least 19 records
All sourcesNASA NTRSDOE OSTI
DOE OSTI2015

Identification of an organic semiconductor superlattice structure of pentacene and perfluoro-pentacene through resonant and non-resonant X-ray scattering

Highly crystalline and stable molecular superlattices are grown with the smallest possible stacking period using monolayers (MLs) of the organic semiconductors pentacene (PEN) and perfluoro-pentacene (PFP). Superlattice reflections in X-ray reflectivity and their energy dependence in resonant soft X-ray reflectivity measurements show that PFP and PEN MLs indeed alternate even though the coherent ordering is lost after ~ 4 ML. The observed lattice spacing of 15.9 Å in the superlattice is larger than in pure PEN and PFP films, presumably because of more upright standing molecules and lack of interdigitation between the incommensurate crystalline PEN and PFP layers. The findings are important for the development of novel organic quantum optoelectronic devices.

36 MATERIALS SCIENCE↗
DOE OSTI2014

Microscopic theory of singlet exciton fission. III. Crystalline pentacene

We extend our previous work on singlet exciton fission in isolated dimers to the case of crystalline materials, focusing on pentacene as a canonical and concrete example. We discuss the proper interpretation of the character of low-lying excited states of relevance to singlet fission. In particular, we consider a variety of metrics for measuring charge-transfer character, conclusively demonstrating significant charge-transfer character in the low-lying excited states. The impact of this electronic structure on the subsequent singlet fission dynamics is assessed by performing real-time master-equation calculations involving hundreds of quantum states. We make direct comparisons with experimental absorption spectra and singlet fission rates, finding good quantitative agreement in both cases, and we discuss the mechanistic distinctions that exist between small isolated aggregates and bulk systems.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
DOE OSTI2015

Structural properties 3,16-bis triisopropylsilylethynyl (pentacene) (TIPS-pentacene) thin films onto organic dielectric layer using slide coating method

3,16-bis triisopropylsilylethynyl (Pentacene) (TIPS-Pentacene) compactable interface property is important in order to have a good arrangement of molecular structure. Comparison for TIPS-Pentacene deposited between two different surface layers conducted. 0.1wt% TIPS-Pentacene diluted in chloroform were deposited onto poly(methylmeaclyrate) (PMMA) layered transparent substrates using slide coating method. X-ray diffraction (XRD) used to determine crystallinity of thin films. Series of (00l) diffraction peaks obtained with sharp first peaks (001) for TIPS-Pentacene deposited onto PMMA layer at 5.35° and separation of 16.3 Å. Morphology and surface roughness were carried out using scanning electron microscope (SEM) and surface profilemeter LS500, respectively.TIPS-Pentacene deposited onto PMMA layer formed needled-like-shape grains with 10.26 nm surface roughness. These properties were related as thin film formed and its surface roughness plays important role towards good mobility devices.

36 MATERIALS SCIENCE↗
DOE OSTI2014

Observation of hole injection boost via two parallel paths in Pentacene thin-film transistors by employing Pentacene: 4, 4″-tris(3-methylphenylphenylamino) triphenylamine: MoO{sub 3} buffer layer

Pentacene organic thin-film transistors (OTFTs) were prepared by introducing 4, 4″-tris(3-methylphenylphenylamino) triphenylamine (m-MTDATA): MoO{sub 3}, Pentacene: MoO{sub 3}, and Pentacene: m-MTDATA: MoO{sub 3} as buffer layers. These OTFTs all showed significant performance improvement comparing to the reference device. Significantly, we observe that the device employing Pentacene: m-MTDATA: MoO{sub 3} buffer layer can both take advantage of charge transfer complexes formed in the m-MTDATA: MoO{sub 3} device and suitable energy level alignment existed in the Pentacene: MoO{sub 3} device. These two parallel paths led to a high mobility, low threshold voltage, and contact resistance of 0.72 cm{sup 2}/V s, −13.4 V, and 0.83 kΩ at V{sub ds} = − 100 V. This work enriches the understanding of MoO{sub 3} doped organic materials for applications in OTFTs.

36 MATERIALS SCIENCE↗
DOE OSTI2018

Highly Contrasting Static Charging and Bias Stress Effects in Pentacene Transistors with Polystyrene Heterostructures Incorporating Oxidizable N , N '-Bis(4-methoxyphenyl)aniline Side Chains as Gate Dielectrics

Charge storage and trapping properties of polymer dielectrics govern the charge densities of adjacent semiconductors and greatly influence the on-off switching voltage (threshold voltage, V th ) of organic field-effect transistors (OFETs) when the polymers are used as gate insulators. Intentional charging of polymer dielectrics in OFETs can change V th and affect the bias stress. We describe a chemical design and fabrication protocol to construct multilayer-stack dielectrics for pentacene-based OFETs using different polystyrene (PS)-based polymers in each layer, with oxidizable N,N-bis(4-methoxyphenyl)anilino (TPAOMe)-substituted styrene copolymers in arbitrary vertical positions in the stacks. Thermal, byproduct-free crosslinking of benzocyclobutene subunits provides integrity to the multilayer structure by preventing dissolution of the previous deposited layer. Neutron reflectivity data verified the multilayer morphology. We compared the Vth shift before and after charging the stacks by application of ±100V across 0.5-1 µm total film thicknesses. Bias stress was the dominant effect in bilayer devices with a TPAOMe layer in contact with the pentacene, indicated by the direction of V th shift associated with either polarity of external electric field. In structures with no TPAOMe subunit in contact with the pentacene, when charging with -100V on top of the source and drain electrodes, electron injection from pentacene to dielectric was the major charging mechanism, again consistent with the bias stress direction. When charging with +100V, bilayer devices without TPAOMe showed little change in V th , suggesting there was no bias stress effect or charge injection in these devices for this charging polarity. For the bilayer devices with the TPAOMe layer in the bottom, and the trilayer devices with TPOMe in the middle, when +100V was applied, the V th shifts were opposite those expected from bias stress. Dipole formation or partial ionization of chargeable groups at the interface between the dielectric layers are likely polarization mechanisms in these cases. A simple analytical model supports the plausibility of these mechanisms. This work provides examples of both stabilization and shifting of V th , and therefore controlling charge carrier density, in semiconductors overlying the dielectric multilayers.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
DOE OSTI2012

Electron transfer beyond the static picture: A TDDFT/TD-ZINDO study of a pentacene dimer

We use time-dependent density functional theory and time-dependent ZINDO (a semi-empirical method) to study transfer of an extra electron between a pair of pentacene molecules. A measure of the electronic transfer integral is computed in a dynamic picture via the vertical excitation energy from a delocalized anionic ground state. With increasing dimer separation, this dynamical measurement of charge transfer is shown to be significantly larger than the commonly used static approximation (i.e., LUMO+1–LUMO of the neutral dimer, or HOMO–LUMO of the charged dimer), up to an order of magnitude higher at 6 Å. These results offer a word of caution for calculations involving large separations, as in organic photovoltaics, where care must be taken when using a static picture to model charge transfer.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
DOE OSTI2022

Unsymmetric Pentacene- and Pentacenequinone-Fused Porphyrins: Understanding the Effect of Cross- and Linear-Conjugation

Unsymmetric pentacenequinone-fused (cross-conjugated) and pentacene-fused (linear-conjugated) porphyrins were designed and synthesized. The cross-conjugated (AM 1 –AM 3 ) and linear-conjugated (AM 5 –AM 7 ) porphyrins displayed strikingly different sets of optical and electronic properties, both of which are unusual and nontypical of porphyrins. MCD, DFT, and TDDFT calculations suggest that multiple charge transfer states exist in both π-conjugated systems, which contributes to the complex absorption and MCD spectra of these molecular systems. The general Gouterman’s four-orbital model used to explain porphyrin spectroscopy led to contradicting theoretical and experimental data, and is thus not applicable for these molecular systems. The “2 + 4” and “3 + 3” active spaces have been deduced and have proven effective to interpret the absorption and MCD spectra of the pentacenequinone-fused (cross-conjugated) and pentacene-fused (linear-conjugated) porphyrins, respectively. Spectroelectrochemistry of AM 5 –AM 7 revealed broad and intense IR absorptions in the range of 1500–2500 nm, illustrating the exceptional ability of these pentacene-fused systems to accommodate positive charges. A pronounced metal effect was observed for pentacene-fused porphyrins. While pentacene-fused Ni(II) porphyrin (AM 6 ) demonstrated an abnormal ability to stabilize pentacene with a half-life of >28.3 days, the half-life of the free base and Zn(II) counterparts were normal, similar to those of pentacene analogues. This work provides important and useful information on guiding new material designs.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
DOE OSTI2015

Fabrication and characterization of 6,13-bis(triisopropylsilylethynyl)-pentacene active semiconductor thin films prepared by flow-coating method

Investigation on the physical characterization and comparison of organic thin film based on a soluble 6,13-bis(triisopropylsilylethynyl) (TIPS) pentacene is reported. Oriented thin-films of pentacene have been successfully deposited by flow-coating method, in which the chloroform solution is sandwiched between a transparent substrate and a slide glass, followed by slow-drawing of the substrate with respect to the slide glass. Molecular orientation of flow-coated TIPS-pentacene is comparable to that of the thermal-evaporated pentacene thin film by the X-ray diffraction (XRD) results. XRD results showed that the morphology of flow-coated soluble pentacene is similar to that of the thermal-evaporated pentacene thin films in series of (00l) diffraction peaks where the (001) diffraction peaks are strongest in the nominally out-of-plane intensity and interplanar spacing located at approximately 2θ = 5.33° (d-spacing, d{sub 001} = 16 Å). Following that, ITO/p-TIPS-pentacene/n-ZnO/Au vertical diode was fabricated. The diode exhibited almost linear characteristics at low voltage with nonlinear characteristics at higher voltage which similar to a pn junction behavior. The results indicated that the TIPS-pentacene semiconductor active thin films can be used as a hole injection layer for fabrication of a vertical organic transistor.

36 MATERIALS SCIENCE↗
DOE OSTI2013

A novel approach for the characterization of a bilayer of phenyl-c71-butyric-acid-methyl ester and pentacene using ultraviolet photoemission spectroscopy and argon gas cluster ion beam sputtering process

The material arrangement and energy level alignment of an organic bilayer comprising of phenyl-c71-butyric-acid-methyl ester (PCBM-71) and pentacene were studied using ultraviolet photoelectron spectroscopy (UPS) and the argon gas cluster ion beam (GCIB) sputtering process. Although there is a small difference in the full width at half maximum of the carbon C 1s core level peaks and differences in the oxygen O 1s core levels of an X-ray photoemission spectroscopy spectra, these differences are insufficient to clearly distinguish between PCBM-71 and pentacene layers and to classify the interface and bulk regions. On the other hand, the valence band structures in the UPS spectra contain completely distinct configurations for the PCBM-71 and pentacene layers, even when they have similar atomic compositions. According to the valence band structures of the PCBM-71/pentacene/electrodes, the highest unoccupied molecular orbital (HOMO) region of pentacene is at least 0.8 eV closer to the Fermi level than that of PCBM-71 and it does not overlap with any of the chemical states in the valence band structure of PCBM-71. Therefore, by just following the variations in the area of the HOMO region of pentacene, the interface/bulk regions of the PCBM/pentacene layers were distinctly categorized. Besides, the variation of valence band structures as a function of the Ar GCIB sputtering time fully corroborated with the surface morphologies observed in the atomic force microscope images. In summary, we believe that the novel approach, which involves UPS analysis in conjunction with Ar GCIB sputtering, can be one of the best methods to characterize the material distribution and energy level alignments of stacks of organic layers.

36 MATERIALS SCIENCE↗
DOE OSTI2014

Trap-induced photoconductivity in singlet fission pentacene diodes

This paper reports a trap-induced photoconductivity in ITO/pentacene/Al diodes by using current-voltage and magneto-conductance measurements. The comparison of photoconductivity between pentacene diodes with and without trap clearly shows that the traps play a critical role in generating photoconductivity. It shows that no observable photoconductivity is detected for trap-free pentacene diodes, while significant photoconductivity is observed in diodes with trap. This is because the initial photogenerated singlet excitons in pentacene can rapidly split into triplet excitons with higher binding energy prior to dissociating into free charge carriers. The generated triplet excitons react with trapped charges to release charge-carriers from traps, leading to a trap-induced photoconductivity in the single-layer pentacene diodes. Our studies elucidated the formation mechanisms of photoconductivity in pentacene diodes with extremely fast singlet fission rate.

75 CONDENSED MATTER PHYSICS, SUPERCONDUCTIVITY AND↗
DOE OSTI2020

Nickel(II) Bisporphyrin‐Fused Pentacenes Exhibiting Abnormal High Stability

Abstract A series of largely π‐extended multichromophoric molecules including cross‐conjugated, half cross‐conjugated, conjugation‐interrupted and linearly conjugated systems were synthesized and characterized. These multichromophoric molecular systems revealed interesting structural‐property relationships. Bisporphyrin‐fused pentacenes Pen‐1 b and Pen‐2 a showed rich redox chemistry with 7 and 8 observable redox states, respectively. The linearly‐conjugated bisporphyrin‐fused pentacenes ( Pen‐1 b and Pen‐2 a ) possess much narrower HOMO–LUMO gaps (1.65 and 1.42 eV redox, respectively) and higher HOMO energy levels than those of their pentacene analogues (2.23 and 2.01 eV redox, respectively), similar to those of much less stable hexacenes and heptacenes. An estimated half‐life of >945 h was obtained for bisporphyrin‐fused pentacene Pen‐2 a , which is much longer than that of its pentacene analogue ( BPE‐P , half‐life, 33 h).

Hu, Yi↗