Journal
JOURNAL OF PHYSICAL CHEMISTRY C
Volume 117, Issue 33, Pages 16759-16768Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jp4033029
Keywords
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Funding
- U.S. Army Research Office [W911NF-09-10472]
- NSF IGERT program [DGE-0903685]
- Roland P. Marquardt Scholarship
- NSFC [21270255]
- NSF-MRI [CHE-1229035, CHE-0722632]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1229035] Funding Source: National Science Foundation
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Introduction of a strong electron-withdrawing dicyanomethylene (-CH-(CN)(2)) group onto a fused bithiophene frame is a useful strategy to convert fused bithiophene derivatives from p-type organic semiconductor materials into n-type materials. Here, through systematic studies of isomerically pure 7-dicyanomethylene-7H-cyclopenta-[1,2-b:4,3-b']dithiophene (1), 4-dicyanomethylene-4H-cyclopenta[2,1-b:3,4-b']dithiophene (2), and 7-dicyanomethylene-7H-cyclopenta[1,2-b:3,4-b']dithiophene (3) as well as their oligomers and polymers, we report that isomerization has the potential to fine-tune the optoelectronic properties of these materials including band gap (E-g), electron affinities (EAs), ionization potentials (IPs), electrochemical polymerization behaviors, and the solid state molecular packing, all of which are important for the performance of semiconductor devices. The monomers of these isomers exhibit noticeable difference in maximum absorption energies; and the oligomers and polymers composed of these monomers exhibit increased band gap difference as predicted by DFT calculation. Furthermore, the isomer 2 exhibits better electrochemical polymerization behavior as well as profound electrochromic switching in the near to middle infrared region. X-ray diffraction and quantum mechanical calculations reveal that the difference of dipole and quadrupole moments in these isomers is likely responsible for the difference in the solid state packing and subsequent polymer assembly.
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