Papers by Ryan Schwiderski
Materials, May 26, 2016
The synthesis, characterization, and electropolymerization of a series of extended fused-ring thi... more The synthesis, characterization, and electropolymerization of a series of extended fused-ring thieno[3,4-b]pyrazine-based terthienyls are reported. The target terthienyls contain a central extended thieno[3,4-b]pyrazine analogue containing 2-thienyl units at the reactive α-positions of the central thiophene. The extended fused-ring thieno[3,4-b]pyrazine analogues studied include acenaphtho[1,2-b]thieno[3,4-e]pyrazine, dibenzo[f,h]thieno[3,4-b]quinoxaline, and thieno[3 1 ,4 1 :5,6]-pyrazino[2,3-f ][1,10]phenanthroline. Comparison of the electrochemical and photophysical properties to simple thieno[3,4-b]pyrazine-based terthienyls and their polymeric analogues are reported in order to provide structure-function relationships within this series of compounds and materials.
Chemical Communications, 2011
The application of fused-ring thieno[3,4-b]pyrazines in conjugated organic polymers has been foun... more The application of fused-ring thieno[3,4-b]pyrazines in conjugated organic polymers has been found to be a powerful approach to the production of low band gap materials. While thieno[3,4-b]pyrazine-based materials date back to the early 1990s, significant advances in the preparation and scope of thieno[3,4-b]pyrazine-based materials have been reported in recent years, primarily in response to the increasing demand for reduced band gap materials in photovoltaic devices. In this review, we provide an overview of thieno[3,4-b]pyrazines and their application to conjugated materials, highlighting in particular the recent advances in the breadth of thieno[3,4-b]pyrazine building blocks and the promise of tuning materials to achieve optimal properties for specific applications.
Synthetic Metals, Jul 1, 2014
ABSTRACT The tunability of the electronic and optical properties of thieno[3,4-b]pyrazine-based t... more ABSTRACT The tunability of the electronic and optical properties of thieno[3,4-b]pyrazine-based terthienyls utilizing electron-donating and electron-withdrawing side chains and their corresponding polymers have been investigated. As previously shown for the thieno[3,4-b]pyrazine monomers, the addition of electron-donating groups results in higher HOMO-LUMO energies in the oligomers and higher Eg values in the resulting polymers. Correspondingly, the use of electron-withdrawing groups provides reduced HOMO-LUMO energies and lower Eg values. The electronic effect of the side chains is diminished in comparison to the thieno[3,4-b]pyrazine analogues. However, the application of electron-withdrawing functionalized thieno[3,4-b]pyrazine-based terthienyls appears to be a promising approach for the production of low Eg materials.
Journal of Heterocyclic Chemistry, May 1, 2012
This review describes the synthesis and characterization of thieno[3,4-b]pyrazines and its extend... more This review describes the synthesis and characterization of thieno[3,4-b]pyrazines and its extended fusedring analogs as important building blocks for the production of low-band gap conjugated materials.
Journal of Organic Chemistry, May 21, 2013
Journal of Organic Chemistry, Jun 29, 2011
Synthetic methods have been developed for the preparation of new 2,3-dihalo- and 2,3-ditriflato-5... more Synthetic methods have been developed for the preparation of new 2,3-dihalo- and 2,3-ditriflato-5,7-bis(2-thienyl)thieno[3,4-<i>b</i>]pyrazines. From these reactive intermediates, a variety of new 2,3-difunctionalized 5,7-bis(2-thienyl)thieno[3,4-<i>b</i>]pyrazines have been produced as precursors to conjugated materials. Structural, electronic, and optical characterization of these new analogues illustrate the extent to which the electronic nature of the functional groups can be used to tune the electronic properties of these thieno[3,4-<i>b</i>]pyrazine-based terthienyl units
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
Synthetic Metals, 2014
ABSTRACT The tunability of the electronic and optical properties of thieno[3,4-b]pyrazine-based t... more ABSTRACT The tunability of the electronic and optical properties of thieno[3,4-b]pyrazine-based terthienyls utilizing electron-donating and electron-withdrawing side chains and their corresponding polymers have been investigated. As previously shown for the thieno[3,4-b]pyrazine monomers, the addition of electron-donating groups results in higher HOMO-LUMO energies in the oligomers and higher Eg values in the resulting polymers. Correspondingly, the use of electron-withdrawing groups provides reduced HOMO-LUMO energies and lower Eg values. The electronic effect of the side chains is diminished in comparison to the thieno[3,4-b]pyrazine analogues. However, the application of electron-withdrawing functionalized thieno[3,4-b]pyrazine-based terthienyls appears to be a promising approach for the production of low Eg materials.
Polymer Bulletin, 2012
A series of 2,3-difunctionalized 5,7-bis(2-thienyl)thieno[3,4-b]pyrazines containing electron-don... more A series of 2,3-difunctionalized 5,7-bis(2-thienyl)thieno[3,4-b]pyrazines containing electron-donating and electron-withdrawing side chains are reported to evaluate the potential tuning effect of the side chains on the electronic properties of these common terthienyl building blocks. In order to further study the resulting effects of such side chains in polymeric materials, the dihexyloxy-functionalized terthienyl was copolymerized with fluorene and its electronic properties compared with a number of analogous materials.
Journal of Heterocyclic Chemistry, 2012
This review describes the synthesis and characterization of thieno[3,4‐b]pyrazines and its extend... more This review describes the synthesis and characterization of thieno[3,4‐b]pyrazines and its extended fused‐ring analogs as important building blocks for the production of low‐band gap conjugated materials.
Chemical Communications, 2011
The application of fused-ring thieno[3,4-b]pyrazines in conjugated organic polymers has been foun... more The application of fused-ring thieno[3,4-b]pyrazines in conjugated organic polymers has been found to be a powerful approach to the production of low band gap materials. While thieno[3,4-b]pyrazine-based materials date back to the early 1990s, significant advances in the preparation and scope of thieno[3,4-b]pyrazine-based materials have been reported in recent years, primarily in response to the increasing demand for reduced band gap materials in photovoltaic devices. In this review, we provide an overview of thieno[3,4-b]pyrazines and their application to conjugated materials, highlighting in particular the recent advances in the breadth of thieno[3,4-b]pyrazine building blocks and the promise of tuning materials to achieve optimal properties for specific applications.
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
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Papers by Ryan Schwiderski