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

Abstract

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.

Tuning the Electronic, Photophysical and Charge Transfer Properties of Small D-a Molecules Based on Thienopyrazine-Terthienyls by Changing the Donor Fragment: A DFT Study

“…This indicates that the compounds TPRi, i=1-3 have a major absorption range (absorb at blue and red shifts) than compound TPR4 (absorb only at red shifts). Furthermore, the difference between wavelengths computed in chloroform and in the gas phase are no more than 27 nm, suggesting that the effect of solvent on the absorption spectra is negligible; which is in agreement with the experimental results for 2,3-disubstitued thieno [3,4-b]pyrazine [51][52].…”

DFT and TD-DFT calculation of new thienopyrazine-based small molecules for organic solar cells

“…Different authors described in recent studies the importance of compounds with D-π-A structure and their role in the elaboration of the organic solar cell [27–29]. The organic material based on thienopyrazine has been used as a donor unit; still receive considerable attention for their exceptional optoelectronic properties [30, 31]. Knowledge about the optoelectronic properties of these new materials can help with the design of new materials with optimized properties for solar energy conversion.…”

Synthesis, Characterization, and Electropolymerization of Extended Fused-Ring Thieno[3,4-b]pyrazine-Based Terthienyls

“…While the majority of TP-based materials utilize various 2,3-difunctionalized TP monomers, a number of extended fused-ring analogues (Figure 2, 3 – 7 ) [36] have also been utilized as potentially improved building blocks in conjugated materials [23,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54]. Such extended fused-ring analogues have included acenaphtho[1,2- b ]thieno[3,4- e ]pyrazines ( 3 ) [37,38,39,40,41,42,43,44,45,46,47], dibenzo[ f,h ]thieno[3,4- b ]quinox-alines ( 4 ) [45,46,47,48,49,50,51], thieno[3′,4′:5,6]pyrazino[2,3- f ][1,10]phenanthroline ( 5 ) [52,53], trithieno[3,4- b :3′,2′- f :2″,3″- h ]quinoxaline ( 6 ) [44,54], and trithieno[3,4- b :2′,3′- f :3″,2″- h ]quinoxaline ( 7 ) [44,54].…”

“…Extended fused-ring TPs are generally applied as stronger acceptors in D-A materials [47], yet these monomers are in reality ambipolar units in the same manner as traditional TPs [35]. As a result, such extended fused-ring TPs are also strong donors and exhibit characteristic internal ICT transitions [36]. …”