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A neutral hexacoordinate silicon complex containing two 2,6-bis(benzimidazol-2′-yl)pyridine (bzimpy) ligands has been synthesized and explored as a potential electron transport layer and electroluminescent layer in organic electronic devices. The air and water stable complex is fluorescent in solution with a λ max = 510 nm and a QY = 57%. Thin films grown via thermal evaporation also fluoresce and possess an average electron mobility of 6.3 × 10 −5 cm 2 V −1 s −1 . An ITO/Si(bzimpy) 2 /Al device exhibits electroluminescence with λ max = 560 nm.
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Pyridine-terminated low gap π-conjugated oligomers: design, synthesis, and photophysical response to protonation and metalation
Reported here is the design and synthesis of among the first pyridine terminated acceptor–donor–acceptor–donor–acceptor (A–D–A–D–A) based π-conjugated oligomers, EH_DPP_2T_Pyr ( 1 ), EH_II_2T_Pyr ( 2 ), and EH_II_1T_Pyr ( 3 ). The molecules incorporate thiophenes as electron donors, isoindigo/diketopyrrolopyrrole as electron acceptors, and are capped with pyridine, a weak electron acceptor, on both ends. All target oligomers show attractive photophysical properties, broad absorption in the visible region ( λ max = 636 nm, 575 nm, and 555 nm, for 1 , 2 , and 3 , respectively) and emission which extends to the IR region (emission λ max = 734 nm and 724 for 1 and 2 , respectively). Given the pyridine nitrogens, the optoelectronic properties of the compounds can be further tuned by protonation/metalation. All compounds show a bathochromic shift in visible absorption and fluorescence quenching upon addition of trifluoroacetic acid (TFA). Similar phenomena are observed upon addition of metals with a particularly strong response to Cu 2+ and Pd 2+ as indicated by Stern–Volmer analysis ( e.g. , for Pd 2+ ; K sv = 7.2 × 10 4 M −1 ( λ = 673 nm), 8.5 × 10 4 M −1 ( λ = 500 nm), and 1.1 × 10 5 ( λ = 425 nm) for 1 , 2 , and 3 , respectively). The selective association of the molecules to Cu 2+ and Pd 2+ is further evidenced by a color change easily observed by eye and under UV light, important for potential use in colorimetric sensing.
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- Award ID(s):
- 1828064
- PAR ID:
- 10295928
- Date Published:
- Journal Name:
- Organic Chemistry Frontiers
- Volume:
- 5
- Issue:
- 21
- ISSN:
- 2052-4129
- Page Range / eLocation ID:
- 3170 to 3177
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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- Free Publicly Accessible Full Text
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Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1039/c8qo00963e
