期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 3, 页码 1014-1025出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo302423p
关键词
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资金
- National Science Foundation [CHE-0832622, CHE-0840431]
- National Institute of Biomedical Imaging and Bioengineering of the National Institutes of Health [1 R15EB008858-01]
- National Academy of Science [PGA-P210877]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0832622] Funding Source: National Science Foundation
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [934212] Funding Source: National Science Foundation
A new series of unsymmetrical diphenylaminofluorene-based chromophores with various strong g-electron acceptors were synthesized and fully characterized. The systematic alteration of the structural design facilitated the investigation of effects such as molecular symmetry and strength of electron-donating and/or -withdrawing termini have on optical nonlinearity. In order to determine the electronic and geometrical properties of the novel compounds, a thorough investigation was carried out by a combination of linear and nonlinear spectroscopic techniques, single-crystal X-ray diffraction, and quantum chemical calculations. Finally, on the basis of two-photon absorption (2PA) cross sections, the general trend for pi-electron accepting ability, i.e., ability to accept charge transfer from diphenylamine was: 2-pyran-4-ylidene malononitrile (pyranone) > dicyanovinyl > bis(dicyanomethylidene)indane >1-(thiophen-2-yl)propenone > dicyanoethylenyl >3-(thiophen-2-yl)propenone. An analogue with the 2-pyran-4-ylidene malononitrile acceptor group exhibited a nearly 3-fold enhancement of the 2PA cross section (1650 GM at 840 nm), relative to other members of the series.
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