Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 13, Pages 6570-6581Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo4007927
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Funding
- 3M Foundation
- National Science Foundation [DMR-0846607]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1229354] Funding Source: National Science Foundation
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [0846607] Funding Source: National Science Foundation
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Six different 2,6-diethyl-4,8-diarylbenzo[1,2-d:4,5-d']bis(oxazoles) and four different 2,4,6,8-tetraarylbenzobisoxazoles were synthesized in two steps: a Lewis acid catalyzed orthoester cyclization followed by a Suzuki or Stille cross-coupling with various arenes. The influence of aryl group substitution and/or conjugation axis variation on the optical and electronic properties of these benzobis(oxazole) (BBO) compounds was evaluated Structural modifications could be used to alter the HOMO, LUMO, and band gap over a range of 1.0, 0.5, and 0.5 eV, respectively. However, depending on the location and identity of the substituent, the HOMO level Can be altered without significantly impacting the LUMO level. This is supported by the calculated frontier molecular orbitals. Our results indicate that the FMOs and band gaps of benzobisoxazoles can be readily modified either jointly or individually.
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