Structure-property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives.

Autor:	Akhmedov TN; Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611, United States., Kumar A; Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611, United States., Starkenburg DJ; Department of Materials Science and Engineering, University of Florida, PO Box 116400, Gainesville, Florida 32611, United States., Chesney KJ; Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611, United States., Abboud KA; Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611, United States., Akhmedov NG; C. Eugene Bennett Department of Chemistry, West Virginia University, 100 Prospect Street, Morgantown, WV 26506, United States.; Department of Chemistry and Biochemistry, The University of Oklahoma, 101 Stephenson Parkway, Norman, OK 73019, United States., Xue J; Department of Materials Science and Engineering, University of Florida, PO Box 116400, Gainesville, Florida 32611, United States., Castellano RK; Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611, United States.
Jazyk:	angličtina
Zdroj:	Beilstein journal of organic chemistry [Beilstein J Org Chem] 2024 May 08; Vol. 20, pp. 1037-1052. Date of Electronic Publication: 2024 May 08 (Print Publication: 2024).
DOI:	10.3762/bjoc.20.92
Abstrakt:	Presented here is the design, synthesis, and study of a variety of novel hydrogen-bonding-capable π-conjugated N -heteroacenes, 1,4-dihydropyrazino[2,3- b ]quinoxaline-2,3-diones (DPQDs). The DPQDs were accessed from the corresponding weakly hydrogen-bonding dicyanopyrazinoquinoxaline (DCPQ) suspensions with excess potassium hydroxide, resulting in moderate to good yields. Both families of compounds were analyzed by UV-vis and NMR spectroscopy, where the consequences of hydrogen bonding capability could be assessed through the structure-property studies. Conversion of the DCPQs into hydrogen-bonding capable DPQDs results in modulation of frontier MO energies, higher molar extinction coefficients, enhanced crystallinity, and on-average higher thermal stability (where in some cases the 5% weight loss temperature is increased by up to 100 °C). Single crystal X-ray diffraction data could be obtained for three DPQDs. One reveals pairwise hydrogen bonding in the solid state as well as a herringbone packing arrangement rendering it a promising candidate for additional studies in the context of organic optoelectronic devices. (Copyright © 2024, Akhmedov et al.)
Databáze:	MEDLINE
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