A Chiroptical Study of Chiral Λ- and X- Type Oligothiophenes Toward Modelling the Interchain Interactions of Chiral Conjugated Polymers

Abstract

A variety of chiral -type and X-type oligothiophenes (MDC 1-10) was synthesized and studied by means of UV-vis and CD spectroscopy in order to model the chiral interchain interactions of conjugated polymers with optically active side chains in both neutral and oxidized state. It was found that, within the class of chiral -type oligothiophenes, the interchain chiral exciton coupling was only present when using an electronwithdrawing imine linkage between the oligothiophene and the chiral unit (MDC 7-9). Together with the observed decrease in g-value (dissymmetry factor for absorption) by extending the oligothiophene moiety, these linkage and elongation restrictions impose crucial drawbacks 2 on chiral -type oligothiophenes as study model in both neutral and oxidized state. Therefore, a new chiral X-type oligothiophene (MDC 10) was developed, which combines chiral exciton coupling in neutral state with the additional ability of oxidation.

A New Chiral Binaphthalene‐Based Fluorescence Polymer Sensor for the Highly Enantioselective Recognition of Phenylalaninol

“…Monomer M ‐ 1 was synthesized according to our previously reported procedure 6e. Monomer M ‐ 2 was first reported by Koeckelbergh and co‐workers8 from the starting material ( S )‐2,2′‐dimethoxy‐1,1′‐binaphthalene in an overall yield of 5 %. Herein, we have significantly improved the synthesis procedures.…”

Tuning of the Electronic Levels of Oligothiophene–Naphthalimide Assemblies by Chemical Modification

“…NAI‐1T‐Br 2 : Under argon atmosphere, a mixture of 4,5‐diamino‐ N ‐2‐hexyldecylnaphthalene‐1,8‐dicarboximide ( 1 ; 100 mg, 0.3 mmol) and of anhydride 2 (92 mg, 0.3 mmol) in glacial acetic acid (10 mL) was heated at reflux for three days. Each 24 h, a further portion of compound 2 (20 mg) was added.…”

Recent Development on Narrow Bandgap Conjugated Polymers for Polymer Solar Cells

“…The substitute (R) could be alkyl chain or aromatic ring, which both provided more rooms to tune the optical property and π-stacking of thieno [3,4-b]pyrrole-4,6-dione-based polymers [69]. In 2010, the Leclerc group and the Jen group reported a thieno [3,4-c]pyrrole-4,6-dione-based polymer (P25, Figure 9) for PSCs at almost same time [70,71]. The polymer P25 contained an octyl-substituted thieno [3,4-c]pyrrole-4,6-dione unit as the acceptor and the 2-ethylhexyoxyl substituted benzodithiophene unit as the donor.…”

“…In contrast, the increment on P27 device was slight with the addition of DIO in the blend solution. The different behavior toward the addition of DIO was In 2010, the Leclerc group and the Jen group reported a thieno [3,4-c]pyrrole-4,6-dione-based polymer (P25, Figure 9) for PSCs at almost same time [70,71]. The polymer P25 contained an octyl-substituted thieno [3,4-c]pyrrole-4,6-dione unit as the acceptor and the 2-ethylhexyoxyl substituted benzodithiophene unit as the donor.…”

“…When blended with PC 70 BM, the solar cell achieved a PCE of 5.77 (Table 2) [86]. In the same year, the Heeger group replaced thiophene with selenophene in a TPD unit to synthesize a new polymer P44 again.…”