biostudies-literatureTalsma WChina Scholarship CouncilScience, Technology and Innovation Commission of Shenzhen MunicipalityChina Postdoctoral Science FoundationNational Natural Science Foundation of ChinaZernike Institute for Advanced Materials, University of GroningenGuangdong Science and Technology Department38056-38066https://www.ebi.ac.uk/biostudies/studies/S-EPMC9412849biostudies-literatureUnknown14(33)Conjugated polymers with narrow band gaps are particularly useful for sorting and discriminating semiconducting single-walled carbon nanotubes (s-SWCNT) due to the low charge carrier injection barrier for transport. In this paper, we report two newly synthesized narrow-band-gap conjugated polymers (PNDITEG-TVT and PNDIC8TEG-TVT) based on naphthalene diimide (NDI) and thienylennevinylene (TVT) building blocks, decorated with different polar side chains that can be used for dispersing and discriminating s-SWCNT. Compared with the mid-band-gap conjugated polymer PNDITEG-AH, which is composed of naphthalene diimide (NDI) and head-to-head bithiophene building blocks, the addition of a vinylene linker eliminates the steric congestion present in head-to-head bithiophene, which promotes backbone planarity, extending the π-conjugation length and narrowing the band gap. Cyclic voltammetry (CV) and density functional theory (DFT) calculations suggest that inserting a vinylene group in a head-to-head bithiophene efficiently lifts the highest occupied molecular orbital (HOMO) level (-5.60 eV for PNDITEG-AH, -5.02 eV for PNDITEG-TVT, and -5.09 eV for PNDIC8TEG-TVT). All three polymers are able to select for s-SWCNT, as evidenced by the sharp transitions in the absorption spectra. Field-effect transistors (FETs) fabricated with the polymer:SWCNT inks display p-dominant properties, with higher hole mobilities when using the NDI-TVT polymers as compared with PNDITEG-AH (0.6 cm2 V-1 s-1 for HiPCO:PNDITEG-AH, 1.5 cm2 V-1 s-1 for HiPCO:PNDITEG-TVT, and 2.3 cm2 V-1 s-1 for HiPCO:PNDIC8TEG-TVT). This improvement is due to the better alignment of the HOMO level of PNDITEG-TVT and PNDIC8TEG-TVT with that of the dominant SWCNT specie.ACS applied materials & interfacesEfficient Selective Sorting of Semiconducting Carbon Nanotubes Using Ultra-Narrow-Band-Gap Polymers.PMC9412849JCYJ20190808160207366617751452020A15151106362020M67277161620106016JCYJ2021032409581002861835009Liu YLoi MADuim HQu JDijkstra SYe GTalsma WTran KSong JChiechi RCfalseEfficient Selective Sorting of Semiconducting Carbon Nanotubes Using Ultra-Narrow-Band-Gap Polymers.Conjugated polymers with narrow band gaps are particularly useful for sorting and discriminating semiconducting single-walled carbon nanotubes (s-SWCNT) due to the low charge carrier injection barrier for transport. In this paper, we report two newly synthesized narrow-band-gap conjugated polymers (PNDITEG-TVT and PNDIC8TEG-TVT) based on naphthalene diimide (NDI) and thienylennevinylene (TVT) building blocks, decorated with different polar side chains that can be used for dispersing and discriminating s-SWCNT. Compared with the mid-band-gap conjugated polymer PNDITEG-AH, which is composed of naphthalene diimide (NDI) and head-to-head bithiophene building blocks, the addition of a vinylene linker eliminates the steric congestion present in head-to-head bithiophene, which promotes backbone planarity, extending the π-conjugation length and narrowing the band gap. Cyclic voltammetry (CV) and density functional theory (DFT) calculations suggest that inserting a vinylene group in a head-to-head bithiophene efficiently lifts the highest occupied molecular orbital (HOMO) level (-5.60 eV for PNDITEG-AH, -5.02 eV for PNDITEG-TVT, and -5.09 eV for PNDIC8TEG-TVT). All three polymers are able to select for s-SWCNT, as evidenced by the sharp transitions in the absorption spectra. Field-effect transistors (FETs) fabricated with the polymer:SWCNT inks display p-dominant properties, with higher hole mobilities when using the NDI-TVT polymers as compared with PNDITEG-AH (0.6 cm2 V-1 s-1 for HiPCO:PNDITEG-AH, 1.5 cm2 V-1 s-1 for HiPCO:PNDITEG-TVT, and 2.3 cm2 V-1 s-1 for HiPCO:PNDIC8TEG-TVT). This improvement is due to the better alignment of the HOMO level of PNDITEG-TVT and PNDIC8TEG-TVT with that of the dominant SWCNT specie.2022-01-01T00:00:00Z2022 Aug2024-11-19T23:58:08.713Z2024-11-19T23:58:08.713ZS-EPMC94128493594338210.1021/acsami.2c07158