Methyl 5′-Chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro-[chromene-2,2′-indoline]-6-carboxylate
Spiropyrans modified with reactive polyfunctional substituents are of great interest as building blocks for the creation of various smart systems with controllable properties for materials science and biomedicine. In this study, a new highly modified spiropyran of the indoline series, methyl 5′-chlo...
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MDPI AG
2023-01-01
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| author | Ilya V. Ozhogin Artem D. Pugachev Anastasia S. Kozlenko Irina A. Rostovtseva Nadezhda I. Makarova Gennady S. Borodkin Islam M. El-Sewify Anatoly V. Metelitsa Boris S. Lukyanov |
| author_facet | Ilya V. Ozhogin Artem D. Pugachev Anastasia S. Kozlenko Irina A. Rostovtseva Nadezhda I. Makarova Gennady S. Borodkin Islam M. El-Sewify Anatoly V. Metelitsa Boris S. Lukyanov |
| author_sort | Ilya V. Ozhogin |
| collection | DOAJ |
| description | Spiropyrans modified with reactive polyfunctional substituents are of great interest as building blocks for the creation of various smart systems with controllable properties for materials science and biomedicine. In this study, a new highly modified spiropyran of the indoline series, methyl 5′-chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro[chromene-2,2′-indoline]-6-carboxylate, was obtained via the cyclocondensation reaction from 5-chloro-1,2,3,3-tetramethyl-3<i>H</i>-indolium perchlorate and methyl 3,5-diformyl-2,4-dihydroxy-benzoate. The molecular structure of the target compound was confirmed by <sup>1</sup>H, <sup>13</sup>C NMR, and IR spectroscopy, as well as LC/MS and elemental analysis. Photochemical studies revealed photochromic activity for the obtained spiropyran at room temperature. The photoinduced merocyanine form demonstrated an enhanced lifetime and fluorescent properties in the red region of the spectrum. |
| first_indexed | 2024-03-11T06:08:43Z |
| format | Article |
| id | doaj.art-d68cf0c78ba14f14b10b02d6d2d518d1 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-11T06:08:43Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-d68cf0c78ba14f14b10b02d6d2d518d12023-11-17T12:49:16ZengMDPI AGMolbank1422-85992023-01-0120231M154910.3390/M1549Methyl 5′-Chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro-[chromene-2,2′-indoline]-6-carboxylateIlya V. Ozhogin0Artem D. Pugachev1Anastasia S. Kozlenko2Irina A. Rostovtseva3Nadezhda I. Makarova4Gennady S. Borodkin5Islam M. El-Sewify6Anatoly V. Metelitsa7Boris S. Lukyanov8Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, RussiaInstitute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, RussiaInstitute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, RussiaInstitute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, RussiaInstitute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, RussiaInstitute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, RussiaInstitute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, RussiaInstitute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, RussiaInstitute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, RussiaSpiropyrans modified with reactive polyfunctional substituents are of great interest as building blocks for the creation of various smart systems with controllable properties for materials science and biomedicine. In this study, a new highly modified spiropyran of the indoline series, methyl 5′-chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro[chromene-2,2′-indoline]-6-carboxylate, was obtained via the cyclocondensation reaction from 5-chloro-1,2,3,3-tetramethyl-3<i>H</i>-indolium perchlorate and methyl 3,5-diformyl-2,4-dihydroxy-benzoate. The molecular structure of the target compound was confirmed by <sup>1</sup>H, <sup>13</sup>C NMR, and IR spectroscopy, as well as LC/MS and elemental analysis. Photochemical studies revealed photochromic activity for the obtained spiropyran at room temperature. The photoinduced merocyanine form demonstrated an enhanced lifetime and fluorescent properties in the red region of the spectrum.https://www.mdpi.com/1422-8599/2023/1/M1549spiropyranphotochromismmolecular switchindolineheterocyclespolyfunctional substituents |
| spellingShingle | Ilya V. Ozhogin Artem D. Pugachev Anastasia S. Kozlenko Irina A. Rostovtseva Nadezhda I. Makarova Gennady S. Borodkin Islam M. El-Sewify Anatoly V. Metelitsa Boris S. Lukyanov Methyl 5′-Chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro-[chromene-2,2′-indoline]-6-carboxylate Molbank spiropyran photochromism molecular switch indoline heterocycles polyfunctional substituents |
| title | Methyl 5′-Chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro-[chromene-2,2′-indoline]-6-carboxylate |
| title_full | Methyl 5′-Chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro-[chromene-2,2′-indoline]-6-carboxylate |
| title_fullStr | Methyl 5′-Chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro-[chromene-2,2′-indoline]-6-carboxylate |
| title_full_unstemmed | Methyl 5′-Chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro-[chromene-2,2′-indoline]-6-carboxylate |
| title_short | Methyl 5′-Chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro-[chromene-2,2′-indoline]-6-carboxylate |
| title_sort | methyl 5 chloro 8 formyl 5 hydroxy 1 3 3 trimethyl spiro chromene 2 2 indoline 6 carboxylate |
| topic | spiropyran photochromism molecular switch indoline heterocycles polyfunctional substituents |
| url | https://www.mdpi.com/1422-8599/2023/1/M1549 |
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