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Spirooxazine photochromic compound
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A photochromic and compound technology, applied in the fields of color-changing fluorescent materials, organic chemistry, chemical instruments and methods, etc.
Inactive Publication Date: 2019-01-15
SUZHOU CHIEN SHIUNG INST OF TECH
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However, there are few studies and applications of spirooxazines in photochromic compounds in the prior art
Method used
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Embodiment 1
[0039] Synthesis of 5-Dimethylamino-1,2,3,3-tetramethyl-3H-indole-1-iodide (I1)
[0040] According to the general method, 4-dimethylaminophenylhydrazine hydrochloride was used as the substrate to obtain the product indole iodide 1, a red solid (yield 48%). 1HNMR (400MHz, CDCl3) δ7.42(d, J=8.6Hz, 1H), 6.89(m, 2H), 4.05(s, 3H), 3.07(s, 6H), 2.92(s, 6H), 1.67( s, 6H). HRMS (ESI) m / z calculated value C14H21N2+=217.1699, detected value was 217.1690.
Embodiment 2
[0042] Synthesis of 1,2,3,3-tetramethyl-5-trifluoromethyl-3H-indole iodide (I2)
[0043] The product indole iodide 2 was obtained as a red solid (50% yield) using 4-trifluoromethylphenylhydrazine hydrochloride as a substrate according to the general method. 1HNMR (400MHz, CDCl3) δ8.02(d, J=2.0Hz, 1H), 7.82(dd, J=8.2,2.0Hz, 1H), 7.92(d, J=8.8Hz, 1H), 3.98(s, 3H), 2.78(s, 3H), 1.62(s, 6H). HRMS (ESI) m / z calculated value C13H15F3N+=242.1151, detected value was 242.1142.
Embodiment 3
[0045] Synthesis of 1,2,3,3-tetramethyl-5-methyl-3H-indole iodide (I3)
[0046] The product indole iodide 3 was obtained as a red solid (yield 56%) using 4-trifluoromethylphenylhydrazine hydrochloride as a substrate according to the general method. 1HNMR (400MHz, CDCl3) δ7.92(d, J=8.6Hz, 1H), 7.21(m, 2H), 4.15(s, 3H), 3.05(s, 3H), 2.41(s, 3H), 1.64( s, 6H). HRMS (ESI) m / z calculated value C13H18N+=188.1434, detected value was 188.1420.
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Abstract
The invention relates to a spirooxazine photochromic compound which has the following general formula (1), wherein R is selected from any one of the group consisting of H, NMe2, Cu (OH) 3, Me and oMe,R' is selected from any one selected from the group consisting of NMe2, CF3, H, NO2 and CN. The spirooxazine photochromic compound is prepared by reacting an indole iodide with a nitroso compound.
Description
technical field [0001] The present invention relates to photochromic compounds, in particular to spirooxazine photochromic compounds. Background technique [0002] Photochromism refers to the reversible conversion process of a chemical species between two forms with significantly different absorption spectra, at least one of which is a light-driven conversion reaction. Photochromism is a new field formed by the intersection of chemistry, physics, materials and optoelectronic technology since the 1990s. In recent years, due to the huge potential applications of photochromic compounds in information storage, ophthalmic lenses, electronic displays, optical switches, etc., photochromic phenomena have become a research hotspot. [0003] At present, most of the researches on photochromic compounds are concentrated on Shiff base, azo compounds, fulgid anhydride, diarylethenes, and related heterocyclic compounds. However, there are few studies and applications of spirooxazine comp...
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