Poly(2,3-dihexylthieno[3,4-<i>b</i>]pyrazine) via GRIM Polymerization: Simple Preparation of a Solution Processable, Low-Band-Gap Conjugated Polymer

Li, Wen; Duck, Benjamin C.; Dastoor, Paul C.; Rasmussen, Seth C.

doi:10.1021/ma801057s

Cited by 82 publications

(85 citation statements)

References 42 publications

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“…In our view, the reduction of the band gap of PCPDT-TP is primarily caused by introducing TP units and less by the alternation of CPDT and TP. This is in accordance with the fact that the band gap of polythienopyrazine (poly-TP) [28,29] is lower than that of PCPDT-TP. Similar www.afm-journal.de Table 2.…”

Section: Redox Propertiessupporting

confidence: 86%

Copolymers of Cyclopentadithiophene and Electron‐Deficient Aromatic Units Designed for Photovoltaic Applications

Bijleveld

Shahid

Gilot

et al. 2009

Adv Funct Materials

149

108

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Alternating copolymers based on cyclopentadithiophene (CPDT) and five different electron‐deficient aromatic units with reduced optical band gaps are synthesized via Suzuki coupling. All polymers show a significant photovoltaic response when mixed with a fullerene acceptor. The frontier orbital levels of the new polymers are designed to minimize energy losses by increasing the open‐circuit voltage with respect to the optical band gap, while maintaining a high coverage of the absorption with the solar spectrum. The best cells are obtained for a copolymer of CPDT and benzooxadiazole (BO) with a band gap of 1.47 eV. This cell gives a short‐circuit current of 5.4 mA cm−2, an open‐circuit voltage of 0.78 V, and a fill factor of 0.6, resulting in a power conversion efficiency of about 2.5%.

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Section: Redox Propertiessupporting

confidence: 86%

Copolymers of Cyclopentadithiophene and Electron‐Deficient Aromatic Units Designed for Photovoltaic Applications

Bijleveld

Shahid

Gilot

et al. 2009

Adv Funct Materials

149

108

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“…Table I collects the bond distances and bond angles optimized at the DFT and CCSD levels using the cc-pVDZ, cc-pVTZ, and aug-ccpVDZ basis sets. Theoretical data are compared with averaged X-ray data obtained from the experimental structures reported by Rasmussen et al for 2,3-dimethyl-TP, 17 2,3-dihexyl-TP, 36 and 2,3-bis͑bromomethyl͒-TP. 37 Table I further includes the computed and microwave geometries 38 of the thiophene molecule for comparison purposes.…”

Section: Resultsmentioning

confidence: 99%

“…The cc-pVTZ basis set indeed provides the best agreement between the computed values and the averaged X-ray data collected in Table I for substituted 2,3-alkyl-TPs. 17,36,37 The comparison between CCSD/cc-pVTZ results and X-ray data …”

Section: Resultsmentioning

confidence: 99%

A theoretical study of the low-lying excited states of thieno[3,4-b]pyrazine

Gómez-Jiménez

Pou-Amérigo

Ortı́

2009

The Journal of Chemical Physics

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The low-lying electronic excited states of thieno͓3,4-b͔pyrazine have been studied using the multiconfigurational second-order perturbation CASPT2 theory with extended atomic natural orbital basis sets. The CASPT2 results allow for a full interpretation of the electronic absorption and emission spectra and provide valuable information for the rationalization of the experimental data. The nature, position, and intensity of the spectral bands have been analyzed in detail. A preliminary comparative study of the ground-state geometry of thieno͓3,4-b͔pyrazine has been performed at the coupled cluster single and doubles and density functional theory levels using a variety of correlation-consistent basis sets. Thieno͓3,4-b͔pyrazine exhibits a polyene-like structure in the ground state due to the bond localization in the pyrazine moiety. An aromatization of the pyrazine unit is predicted for the lowest-energy electronic excited states.

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“…The GRIM method also represents an easy synthetic route to afford the low-band-gap poly(thieno [3,4-b]pyrazine)s (PTPs) P64 [92] (Scheme 35). In this case moderate yields (50-55 %) were obtained under reflux conditions.…”

Section: Microreviewmentioning

confidence: 99%

Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production

et al. 2014

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Bequeme Routine: Mehrlagige dünne Polymerfilme wurden durch Elektrophorese auf in Agarose immobilisierten Partikeln angeordnet. Anschließendes Entfernen des Kerns führte zu robusten Kapseln mit unterschiedlichen Polymerzusammensetzungen (siehe Fluoreszenzbild). Dieser Ansatz ermöglicht den vielseitigen und routinemäßigen Aufbau von nano‐ und mikroskaligen Kapseln sowie beschichteten Partikeln in sehr wenigen Prozessschritten.

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Poly(2,3-dihexylthieno[3,4-b]pyrazine) via GRIM Polymerization: Simple Preparation of a Solution Processable, Low-Band-Gap Conjugated Polymer

Cited by 82 publications

References 42 publications

Copolymers of Cyclopentadithiophene and Electron‐Deficient Aromatic Units Designed for Photovoltaic Applications

Copolymers of Cyclopentadithiophene and Electron‐Deficient Aromatic Units Designed for Photovoltaic Applications

A theoretical study of the low-lying excited states of thieno[3,4-b]pyrazine

Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production

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