Structural Effects on the Electronic Properties of Extended Fused-Ring Thieno[3,4-b]pyrazine Analogues

• Published in: Journal of organic chemistry Vol. 76; no. 15; pp. 6383 - 6388
• Main Authors: Nietfeld, Jon P, Schwiderski, Ryan L, Gonnella, Thomas P, Rasmussen, Seth C
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 05.08.2011; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Electrochemistry; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; RAMAN-SPECTRA; POLYMERS; POLY(THIOPHENES); SOLAR-CELLS; DONOR; LOW-BAND-GAP; POLYMERIZATION; NARROW-BANDGAP; COPOLYMER; GREEN; Characterization; Structure effect; Sulfur heterocycle; Electronic properties; Nitrogen heterocycle; Optical properties; Electrochemistry; Chemical synthesis; Structure function relationship
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo200850w

The synthesis and characterization of the extended thieno[3,4-b]pyrazine analogues acenaphtho[1,2-b]thieno[3,4-e]pyrazine (3a), 3,4-dibromoacenaphtho[1,2-b]thieno[3,4-e]pyrazine (3b), 3-octylacenaphtho[1,2-b]thieno[3,4-e]pyrazine (3c), dibenzo[f,h]thieno[3,4-b]quinoxaline (4), and thieno[3′,4′:5,6]pyrazino[2,3-f][1,10]phenanthroline (5) are reported. Comparison of structural, electrochemical, and photophysical properties to those of simple thieno[3,4-b]pyrazines are provided in order to provide structure–function relationships within this series of compounds.