Synthesis and characterization of photochromic indolyl substituted fulgides and fulgimides

The fulgide and fulgimide family constitutes an important class of organic photochromic compounds. The ability of fulgides and fulgimides to interconvert between two key forms by irradiation of different wavelength of light has made them promising material in optical memory devices, optical switches and sensors, and specialty dyes and inks. Thermal stability and hydrolytic stability of fulgides and fulgimides are essential for their practical applications. A deuterated trifluoromethyl indolylfulgide was synthesized based on the synthetic pathway of the proteo trifluoromethyl indolylfulgide using commercially available deuterated starting materials. Deuteration of the isopropylidene group improved the thermal stability of the indolylfulgide by a factor of 7. ^ Fulgimides are the most important fulgide derivatives. Fulgimides improve the hydrolytic stability of fulgides by replacing the succinic anhydride ring with a succinimide ring. A novel trifluoromethyl N-ethoxycarbonylmethyl indolylfulgimide was synthesized from trifluoromethyl indolylfulgide. The trifluoromethyl indolylfulgide was synthesized on a large scale in five steps with an overall yield of 18%. The indolylfulgide was then converted to indolylfulgimide by aminolysis follow by dehydration. The N-ethoxycarbonylmethyl indolylfulgimide showed enhanced hydrolytic stability and photochemical stability in 70/30 ethanol/water. ^ Three novel aqueous soluble fulgimides, trifluoromethyl carboxylic acid indolylfulgimide, dicarboxylic acid indolylfulgimide, and H-carboxylic acid indolylfulgimide, were synthesized. In sodium phosphate buffer (pH 7.4) at 37 ºC, an unusual hydrolysis of the trifluoromethyl group of the closed form of the carboxylic acid indolylfulgimide resulted in the dicarboxylic acid indolylfulgimide which has an additional carboxylic acid group. The closed form of dicarboxylic acid indolylfulgimide was further decarboxylated to generate H-carboxylic acid indolylfulgimide which was not photochromic. The trifluoromethyl dicarboxylic acid indolylfulgimide is the most robust fulgimide yet reported in aqueous solution. ^ A novel aqueous soluble methyl carboxylic acid indolylfulgimide was synthesized from methyl indolylfulgide. The methyl indolylfulgide was synthesized in five steps with an overall yield of 21%. The methyl carboxylic acid indolylfulgimide was synthesized by aminolysis follow by dehydration. The methyl carboxylic acid indolylfulgimide is expected to have improved thermal and photochemical stability in aqueous solutions relative to the trifluoromethyl analog.^

Initial placement methods for Haitian adult ESOL students : the NYS place test plus profile data compared to subjective assessment

Few valid and reliable placement procedures are available to assess the English language proficiency of adults who enroll in English for Speakers of Other Languages (ESOL) programs. Whereas placement material exists for children and university ESOL students, the needs of students in adult community education programs have not been adequately addressed. Furthermore, the research suggests that a number of variables, such as, native language, age, prior schooling, length of residence, and employment are related to second language acquisition. Numerous studies contribute to our understanding of the relationship of these factors to second language acquisition of Spanish-speaking students. Again, there is a void in the research investigating the factors affecting second language acquisition and consequently, appropriate placement of Haitian Creole-speaking students. This study compared a standardized instrument, the NYS Place Test, used alone and in combination with a writing sample in English, to subjective judgement of a department coordinator for initial placement of Haitian adult ESOL students in a community education program. The study also investigated whether or not consideration of student profile data improved the accuracy of the test. Finally, the study sought to determine if a relationship existed between student profile data and those who withdrew from the program or did not enter a class after registering. Analysis of the data by crosstabulation and chi-square revealed that the standardized NYS Place Test was at least as accurate as subjective department coordinator placement and that one procedure could be substituted for li other. Although the writing sample in English improved accuracy of placement by the NYS test, the results were not significant. Of the profile variables, only length of residence was found to be significantly related to accuracy of placement using the NYS Place Test. The number of incorrect placements was higher for those students who lived in the host country from twenty-five to one hundred ten months. A post hoc analysis of NYS test scores according to level showed that those learners who placed in level three also had a significantly higher incidence of incorrect placements. No significant relationship was observed between the profile variables and those who withdrew from the program or registered but did not enter a class.