Strategies for Electrooptic Film Fabrication. Influence of Pyrrole-Pyridine-Based Dibranched Chromophore Architecture on Covalent Self-Assembly, Thin-Film Microstructure, and Nonlinear Optical Response
The new dibranched, heterocyclic 'push-pull' chromophores bis{l_brace}1-(pyridin-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane{r_brace}methane (1), 1-(pyrid-4-yl)-2-(N-methyl-5-formylpyrrol-2-yl)ethylene (2), {l_brace}1-(N-methylpyridinium-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane{r_brace}{l_brace}[1-(pyridin-4-yl)-2-[2-(N-methylpyrrol-5-yl)]ethane]{r_brace}methane (3), N-methyl-2-[1-(N-methylpyrid-4-yl)ethen-2-yl]-5-[pyrid-4-yl]ethen-2-yl-pyrrole iodide (4), bis{l_brace}1-(N-methyl-4-pyridinio)-2-[2-(N-methylpyrrol-5-yl)]ethane{r_brace}methane iodide (5), and N-methyl-2,5-[1-(N-methylpyrid-4-yl)ethen-2-yl]pyrrole iodide (6) have been synthesized and characterized. The neutral (1 and 2) and monomethyl salts (3 and 4) undergo chemisorptive reaction with iodobenzyl-functionalized surfaces to afford chromophore monolayers SA-1/SA-2 and SA-3/SA-4, respectively. Molecular structures and other physicochemical properties have been defined by 1H NMR, optical spectroscopy, and XRD. Thin-film characterization by a variety of techniques (optical spectroscopy, specular X-ray reflectivity, atomic force microscopy, X-ray photoelectron spectroscopy, and angle-dependent polarized second harmonic generation) underscore the importance of the chromophore molecular architecture as well as film growth method on film microstructure and optical/electrooptic response.
- Research Organization:
- Brookhaven National Laboratory (BNL) National Synchrotron Light Source
- Sponsoring Organization:
- Doe - Office Of Science
- DOE Contract Number:
- AC02-98CH10886
- OSTI ID:
- 914247
- Report Number(s):
- BNL--78815-2007-JA
- Journal Information:
- J. Am. Chem. Soc., Journal Name: J. Am. Chem. Soc. Vol. 128; ISSN JACSAT; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
Similar Records
Design and synthesis of orally bioavailable serum and glucocorticoid-regulated kinase 1 (SGK1) inhibitors
3-D indium(III)-btc channel frameworks and their ion-exchange properties (btc=1,3,5-benzenetricarboxylate)