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The electronic structure and molecular orientation of semiconducting polymers in thin films determine their ability to transport charge. Methods based on near-edge X-ray absorption fine structure NEXAFS spectroscopy can be used to probe both the electronic structure and microstructure of semiconducting polymers in both crystalline and amorphous films. However, it can be challenging to interpret NEXAFS spectra on the basis of experimental data alone, and accurate, predictive calculations are needed to complement experiments.
Core-level X-ray absorption spectra of a set of semiconducting polymers were calculated using the excited electron and core-hole XCH approach based on constrained-occupancy DFT.
A comparison of calculations on model oligomers and periodic structures with experimental data revealed the requirements for accurate prediction of NEXAFS spectra of both conjugated homopolymers and donor—acceptor polymers.
The NEXAFS spectra predicted by the XCH approach were applied to study molecular orientation in donor—acceptor polymers using experimental spectra and revealed the complexity of using carbon edge spectra in systems with large monomeric units.
The XCH approach has sufficient accuracy in predicting experimental NEXAFS spectra of polymers that it should be considered for design and analysis of measurements using soft X-ray techniques, such as resonant soft X-ray scattering and scanning transmission X-ray microscopy.
Figure 1. Density distributions of the electronic component of the first core-excited state analogous to the lowest unoccupied molecular orbital overlay the molecular models. The excited atom is shown in green. Figure 2. Figure 3. Simulated isotropic spectra of a sexithiophene model with varying side chain lengths, designated by the R group in the schematic.
Note the side chains are fully extended in these models. All of the carbon atoms on the attached side chains were excited if present.
The filled traces show the individual contributions from the four different carbon atoms on the thiophene units. It is clear that the lowest energy transition of the carbon atom bonded directly to the R group shifts to higher energy in the presence of an alkyl side chain, as shown by the filled purple trace.
Figure 4. For the XCH-predicted isotropic absorption profile, contributions from four exemplary carbon atoms are shown, in addition to the overall spectra. These specific atoms are labeled and color-coded on the molecular structure. Figure 5. For the calculations, the PCDTPT model compound CDT—PT—CDT—PT was assumed to be perfectly aligned along the chain axis and oriented with the conjugated backbone plane perpendicular to the substrate, as shown in part a, and the electric field vector direction changed within the y — z plane.
Experimental plots shown are surface-sensitive partial electron yield data for a PCDTPT sample that was aligned using blade-coating, 57 which mimics the model system and geometry used for the calculations. Experimental spectra were previously reported in ref Figure 6. Simulated and experimental data for the carbon K-edge of a thiophene-based system.
Experimental plots shown are surface-sensitive partial electron yield data of P3HT. Simulated spectra are for a sexi 3-hexylthiophene model with conjugated backbone planes perpendicular to the substrate, unidirectional chain axis alignment, and fully extended, linear side chains.
Figure 7. The NDI unit was assumed to be perfectly edge-on, i. The angle-dependent spectra of the entire repeat unit is shown in purple traces top , and carbon atoms only on the NDI unit are shown in the blue traces middle. Angle-dependent spectra of the thiophene atoms are shown as the orange traces bottom.
The intensities of the transitions in each panel were independently normalized. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information.
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Department of Energy under Contract No. The authors thank Daniel A. The authors thank Andrew McGuan for help with automating angle-dependent results. C , , 17 , More by Gregory M. More by Shrayesh N. More by C. More by David Prendergast. More by Michael L. Cite this: J. C , , 17 , — ACS AuthorChoice.
Article Views Altmetric -. Citations 9. Abstract High Resolution Image. Semiconducting polymers are promising materials for flexible organic electronics.
Interpretation of transport measurements requires information about the molecular packing and orientation of semiconducting polymers in the direction of transport.
In addition to their bulk structure, the thin film geometry of most organic electronic devices makes the microstructure at surfaces and interfaces equally important. Many polymers are highly ordered, allowing both X-ray diffraction 5,6 and electron microscopy 7,8 to reveal details of their microstructure, but many emerging materials are noncrystalline.
Near-edge X-ray absorption fine structure NEXAFS spectroscopy can reveal molecular orientation and ordering by probing element-specific electronic transitions of core level electrons to unoccupied molecular orbitals. Assignment of the features in NEXAFS spectra of conjugated materials, however, can be complex due to the delocalization of unoccupied electronic levels. This methodology provides a means to capture the unique electronic structure of semiconducting polymers, particularly for computations of periodic structures, and can provide insight into interpretation of soft X-ray-based experimental studies.
NEXAFS spectroscopy, microscopy, and scattering methods have been used extensively to study molecular organic materials and polymers. The interpretation of the features observed in NEXAFS spectra of organic molecules is often based on the building-block model, where complex molecular compounds are regarded as being composed of local subunits 10,13,30 the independent features of which can be summed together to form the overall spectrum.
However, this model can fail to capture the detailed spectral features of molecules in the solid state. For example, quantitative interpretation of NEXAFS spectra could help elucidate connections between excited state delocalization and the formation of free charges versus excitons, which is still not well-understood.
Quantum chemical models to calculate the X-ray absorption spectra of organic materials have been developed and applied to molecular materials and polymers and have been able to describe the nature of observed NEXAFS transitions. XCH has already been shown to work well for systems containing small organic molecules or periodic systems, such as graphene. We show how the predicted NEXAFS spectra of polythiophenes evolve as a function of the number of polymer repeat units and the length of attached side chains.
These benchmark calculations provide guidance for using the XCH methodology with techniques such as PSoXS and STXM to characterize semiconducting polymer films where a detailed understanding of X-ray absorption is required for detailed analysis.
Experimental and Computational Methods. The molecular geometry of polymers were modeled as oligomers containing a specific number of repeat units with methyl groups typically replacing full hydrocarbon side chains, unless otherwise noted.
The distance between the ends of the desired repeat unit was measured, and the additional end units were removed. For example, a sexithiophene-based unit was used as the repeating unit cell in a simplified model of poly thiophene Figure S1 , SI , even though a similar repeating structure can be obtained based on a bithiophene unit cell. This was done because in the XCH calculations, which employ periodic boundary conditions, the specified excited atom is one of an infinite array of excited atoms in every unit cell, and a critical unit size is needed to avoid simultaneously exciting atoms very close to each other.
For this study, the atom coordinates remained fixed during computations. In the XCH method, the lowest energy excited state of the core-hole is accounted for by replacing the pseudopotential of the core-excited atom with a core-hole pseudopotential that explicitly includes the core excitation.
The screening presence of the excited electron is also included. Higher energy states are estimated relative to the lowest core-excited reference state based on the unoccupied portion of the Kohn—Sham DFT eigenspectrum.
The core excitation is moved from atom to atom of the same element, and the resulting simulated XAS spectrum is accumulated. Energy alignment was determined on the basis of a previous method that references excited states to theoretical isolated atoms. Note that these constant shifts are determined on the basis of alignment to specific standards, independent of the current study. Therefore, a dilation factor of 1. Simulated transitions are numerically convoluted with a Gaussian line shape with peak widths of 0.
A spherical grating monochromator was used to select soft X-rays in the range from to eV, encompassing the carbon and nitrogen K-edges.
All experiments were done in an ultrahigh vacuum UHV chamber. Carbon edge PEY data were normalized by subtracting a linear pre-edge baseline and setting the edge jump to unity at eV. For nitrogen K-edge experiments, a single scan was done at energies comprising the carbon K-edge and the nitrogen K-edge. After normalizing the carbon K-edge, nitrogen K-edge data were normalized by fitting the post carbon edge decay to an exponential and subtracting this baseline from the nitrogen edge energies.
Total electron yield was determined on the basis of the neutralization current. Results and Discussion. The electronic wave functions in conjugated oligomers and polymers are often delocalized over many repeat units; 60 therefore, it is important to know if calculations using smaller fragments, which can reduce computational times, can provide an adequate description of NEXAFS spectra.
The size of the fragment will vary depending on the structure of the polymer, as is well-known for calculations of the optical band gap of homopolymers such as polythiophene. Such an ability will be particularly helpful to predict changes in transition energies between highly ordered and disordered polymer chains with differing conjugation lengths.
We examined the evolution of XCH-predicted spectra as a function of chain length for models of polythiophene and found that intermediate-sized fragments are suitable for simulating experimental NEXAFS spectra.
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