Hydrogen-Bonding Trends in a Bithiophene with 3- and/or 4‑Pyridyl Substituents

To improve the charge-carrier transport capabilities of thin-film organic materials, the intermolecular electronic couplings in the material should be maximized. Decreasing intermolecular distance while maintaining proper orbital overlap in highly conjugated aromatic molecules has so far been a succ...

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Veröffentlicht in:ACS omega 2023-07, Vol.8 (27), p.24485-24494
Hauptverfasser: Costello, Alison M., Duke, Rebekah, Sorensen, Stephanie, Kothalawala, Nadeesha L., Ogbaje, Moses, Sarkar, Nandini, Kim, Doo Young, Risko, Chad, Parkin, Sean R., Huckaba, Aron J.
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container_end_page 24494
container_issue 27
container_start_page 24485
container_title ACS omega
container_volume 8
creator Costello, Alison M.
Duke, Rebekah
Sorensen, Stephanie
Kothalawala, Nadeesha L.
Ogbaje, Moses
Sarkar, Nandini
Kim, Doo Young
Risko, Chad
Parkin, Sean R.
Huckaba, Aron J.
description To improve the charge-carrier transport capabilities of thin-film organic materials, the intermolecular electronic couplings in the material should be maximized. Decreasing intermolecular distance while maintaining proper orbital overlap in highly conjugated aromatic molecules has so far been a successful way to increase electronic coupling. We attempted to decrease the intermolecular distance in this study by synthesizing cocrystals of simple benzoic acid coformers and dipyridyl-2,2′-bithiophene molecules to understand how the coformer identity and pyridine N atom placement affected solid-state properties. We found that with the 5-(3-pyridyl)-5′-(4-pyridyl)-isomer, the 4-pyridyl ring interacted with electrophiles and protons more strongly. Synthesized cocrystal powders were found to have reduced average crystallite size in reference to the parent compounds. The opposite was found for the intermolecular electronic couplings, as determined via density functional theory (DFT) calculations, which were relatively large in some of the cocrystals.
doi_str_mv 10.1021/acsomega.3c02423
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title Hydrogen-Bonding Trends in a Bithiophene with 3- and/or 4‑Pyridyl Substituents
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