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Lone-Pair Delocaliz...
Lone-Pair Delocalization Effects within Electron Donor Molecules: The Case of Triphenylamine and Its Thiophene-Analog
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- Zhang, Teng, 1988- (author)
- Uppsala universitet,Molekyl- och kondenserade materiens fysik,Uppsala Univ, Dept Phys & Astron, Box 516, SE-75120 Uppsala, Sweden.
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- Brumboiu, Iulia E., 1987- (author)
- KTH,Teoretisk kemi och biologi,KTH Royal Institute of Technology, Department of Theoretical Chemistry and Biology & Korea Advanced Institute of Science and Technology (KAIST), Department of Chemistry
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- Grazioli, Cesare (author)
- ISM-CNR, Trieste LD2 Unit, Italy,Sincrotrone Trieste, CNR, ISM, I-34149 Trieste, Basovizza, Italy.
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- Guarnaccio, Ambra (author)
- ISM-CNR, Tito Scalo (Pz), Italy,CNR, ISM, I-85050 Potenza, Italy.
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- Coreno, Marcello (author)
- ISM-CNR, Trieste LD2 Unit, Italy,Sincrotrone Trieste, CNR, ISM, I-34149 Trieste, Basovizza, Italy.
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- de Simone, Monica (author)
- IOM-CNR, Laboratorio TASC, Sincrotrone Trieste, Basovizza, Trieste, Italy,Sincrotrone Trieste, Lab TASC, CNR, IOM, I-34149 Trieste, Basovizza, Italy.
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- Santagata, Antonio (author)
- ISM-CNR, Tito Scalo (Pz), Italy,CNR, ISM, I-85050 Potenza, Italy.
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- Rensmo, Håkan (author)
- Uppsala universitet,Molekyl- och kondenserade materiens fysik,Uppsala Univ, Dept Phys & Astron, Box 516, SE-75120 Uppsala, Sweden.
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- Brena, Barbara (author)
- Uppsala universitet,Materialteori,Uppsala Univ, Dept Phys & Astron, Box 516, SE-75120 Uppsala, Sweden.
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- Lanzilotto, Valeria (author)
- Uppsala universitet,Molekyl- och kondenserade materiens fysik,Uppsala Univ, Dept Phys & Astron, Box 516, SE-75120 Uppsala, Sweden.
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- Puglia, Carla (author)
- Uppsala universitet,Molekyl- och kondenserade materiens fysik,Uppsala Univ, Dept Phys & Astron, Box 516, SE-75120 Uppsala, Sweden.
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(creator_code:org_t)
- 2018-07-12
- 2018
- English.
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In: The Journal of Physical Chemistry C. - : American Chemical Society (ACS). - 1932-7447 .- 1932-7455. ; 122:31, s. 17706-17717
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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https://urn.kb.se/re...
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Abstract
Subject headings
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- Triphenylamine (TPA) and its thiophene-analog, N,N-diphenyl-2-thiophenamine (DPTA), are both well-known as electron-donating molecules implemented in optoelectronic devices such as organic solar cells and LEDs. Comprehensive valence and core level photoelectron spectroscopy, as well as near edge X-ray absorption spectroscopy (NEXAFS), measurements have been performed on gas phase TPA and DPTA. The experimental results have been compared to density functional theory calculations, providing a detailed description of the molecular electronic structure. Specifically, the C 1s photoelectron lines of both TPA and DPTA were resolved in the different C atom contributions and their binding energies explained as the result of two counter-acting effects: (1) the electronegativity of the nitrogen atom (and sulfur atom in DPTA) and (2) the the N (and S in DPTA) lone-pair electrons. In addition, the C K-edge NEXAFS spectrum of DPTA reveals that the lowest unoccupied molecular orbital (LUMO) energy position is affected differently if the core hole site is on the phenyl compared to the thiophene ring. The electron-donating properties of these two molecules are largely explained by the significant contribution of the N lone-pair electrons (p(z)) to the highest occupied molecular orbital. The contribution to the LUMO and to the empty density of states of the sulfur of the thiophene ring in DPTA explains the better performance of donor-pi-acceptor molecules containing this moiety and implemented in photoenergy conversion devices.
Subject headings
- NATURVETENSKAP -- Fysik (hsv//swe)
- NATURAL SCIENCES -- Physical Sciences (hsv//eng)
- NATURVETENSKAP -- Kemi -- Teoretisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Theoretical Chemistry (hsv//eng)
- NATURVETENSKAP -- Fysik -- Den kondenserade materiens fysik (hsv//swe)
- NATURAL SCIENCES -- Physical Sciences -- Condensed Matter Physics (hsv//eng)
Keyword
- Physics with spec. in Atomic, Molecular and Condensed Matter Physics
- Fysik med inriktning mot atom- molekyl- och kondenserande materiens fysik
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Zhang, Teng, 198 ...
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Brumboiu, Iulia ...
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Grazioli, Cesare
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Guarnaccio, Ambr ...
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Coreno, Marcello
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de Simone, Monic ...
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Santagata, Anton ...
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Rensmo, Håkan
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Brena, Barbara
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Lanzilotto, Vale ...
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Puglia, Carla
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- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Physical Science ...
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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and Theoretical Chem ...
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Physical Science ...
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and Condensed Matter ...
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Uppsala University
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Royal Institute of Technology