RESUMO
A novel chelatofore functionalized spiropyran of the 2-oxaindane series, namely 8-formyl-7-hydroxy-3',3'-dimethylspiro[2H-chromene-2,1'(3'H)-2-benzofuran], C(19)H(16)O(4), is reported. In the crystalline state, dimers are formed as a result of the pi-pi stacking of aromatic groups of the 2H-chromene part of the molecule and C-H...O interactions. The C(spiro)-O bond length in the pyran ring is 1.4558 (10) A, which is longer than or equal to the bond length in thermo- and photochromic 2-oxaindane spiropyrans synthesized previously, except for the 7,8-benzo/6-NO(2) derivative, in which this bond length is 1.465 (2) A.
RESUMO
Six novel functionalized spiropyran's derivatives of 2H-1,3-benzoxazinone series were synthesized by introducing the substituents with chelating ability into 2H-chromene part of the 8'-formyl-7'-hydroxy-3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazine-2-spiro-2'-[2H]-chromene (I) by condensation with 2-aminophenol, 2-amino-4-methylphenol, 2-amino-4-nitrophenol, 2-amino-1-methylbenzimidazole, 4-amino-4H-1,2,4-triazole, N-(4-aminophenyl)acetamide. (1)H NMR, UV/vis, IR spectroscopy combined with quantum-chemical calculations employing density functional theory (DFT) were used to study their structure. All substances, except 2-amino-4-nitrophenol derivative exist in solid state and in solution solely in closed spiroform, while the mentioned one undergoes partial spiropyran ring opening. In DMSO solution NMR spectra show ratio of 2:1 of closed and opened form, correspondingly.
