Taming hot CF3 radicals: incrementally tuned families of polyarene acceptors for air-stable molecular optoelectronics
Breakthroughs in molecular optoelectronics await the availability of new families of air-stable polyaromatic hydrocarbon (PAH) acceptors with incrementally- and predictably-tunable electron affinities and structures capable of inducing desirable solid-state morphologies in hybrid materials. Although the addition of electron withdrawing groups to PAHs has been studied for decades, producing new compounds from time to time, a generic one-step synthetic methodology applicable to potentially all PAH substrates has been, until now, an impossible dream. We herein report that at least seventeen common PAHs and polyheterocyclics can be trifluoromethylated by a new procedure to yield families of PAH(CF3)n acceptors with (i) n = 4-8, (ii) multiple isomers for particular n values, (iii) gas-phase experimental electron affinities as high as 3.32 eV and shifted from the respective PAH precursor as a linear function of n, and (iv) various solid-state morphologies, including the ability to form alternating π stacked hybrid crystals with aromatic donors.
- Research Organization:
- Pacific Northwest National Laboratory (PNNL), Richland, WA (US), Environmental Molecular Sciences Laboratory (EMSL)
- Sponsoring Organization:
- USDOE
- DOE Contract Number:
- AC05-76RL01830
- OSTI ID:
- 1088620
- Report Number(s):
- PNNL-SA-93035; 46893; KC0301020
- Journal Information:
- Angewandte Chemie International Edition, 52(18):4871-4874, Journal Name: Angewandte Chemie International Edition, 52(18):4871-4874
- Country of Publication:
- United States
- Language:
- English
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