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<p>Knudsen effusion mass spectrometry technique was used to investigate the crystal-vapor or liquid–vapor equilibrium for certain indoline-based spiropyrans with formyl substituents: 1,3,3-trimethyl-6´-etoxi-8´-formyl-spiro[indoline-2,2´-<i>2H</i>-chromene] (<Emphasis Type="BoldItalic">2</Emphasis>), 1,3,3-trimethyl-6´-metoxicarbonyl-8´-formyl-spiro[indoline-2,2´-<i>2H</i>-chromene (<Emphasis Type="BoldItalic">3</Emphasis>), 1,3,3-trimethyl-8´-allyl-6´-formyl-spyro[indoline-2,2´-<i>2H</i>-chromene] (<Emphasis Type="BoldItalic">5</Emphasis>), and 1,3,3-trimethyl-8´-benzyl-6´-formyl-spiro[indoline-2,2´-<i>2H</i>-chromene] (<Emphasis Type="BoldItalic">6</Emphasis>). The temperature dependencies of their vapor pressures were used to derive sublimation enthalpies, Δ<sub>sub</sub><i>H</i>°(298.15&#xa0;K)/kJ&#xa0;mol<sup>–1</sup>, as 131 ± 4, 136 ± 4, 134 ± 5, and 130 ± 8 for compounds <Emphasis Type="BoldItalic">2</Emphasis>, <Emphasis Type="BoldItalic">3</Emphasis>, <Emphasis Type="BoldItalic">5</Emphasis>, and <Emphasis Type="BoldItalic">6</Emphasis>, respectively. These values together with the previously obtained data for other indoline-based spiropyrans were analyzed to reveal the effect of substituents in positions 6′ and 8′ on sublimation enthalpy. The obtained results are the basis for the industrial application of these photochromic materials using vapor phase.</p>

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Thermodynamic properties of indoline-based spiropyrans: effect of substituents in positions 6’ and 8’ on sublimation enthalpy

  • 期刊论文

  • 发表日期：

    2025年6月2日

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  • Vladimir B. Motalov,
  • Anatoliy M. Dunaev,
  • Andrey S. Kaplin,
  • Lev S. Kudin,
  • Artem D. Pugachev,
  • Gennady S. Borodkin,
  • Ilya V. Ozhogin

摘要

Knudsen effusion mass spectrometry technique was used to investigate the crystal-vapor or liquid–vapor equilibrium for certain indoline-based spiropyrans with formyl substituents: 1,3,3-trimethyl-6´-etoxi-8´-formyl-spiro[indoline-2,2´-2H-chromene] (2), 1,3,3-trimethyl-6´-metoxicarbonyl-8´-formyl-spiro[indoline-2,2´-2H-chromene (3), 1,3,3-trimethyl-8´-allyl-6´-formyl-spyro[indoline-2,2´-2H-chromene] (5), and 1,3,3-trimethyl-8´-benzyl-6´-formyl-spiro[indoline-2,2´-2H-chromene] (6). The temperature dependencies of their vapor pressures were used to derive sublimation enthalpies, ΔsubH°(298.15 K)/kJ mol–1, as 131 ± 4, 136 ± 4, 134 ± 5, and 130 ± 8 for compounds 2, 3, 5, and 6, respectively. These values together with the previously obtained data for other indoline-based spiropyrans were analyzed to reveal the effect of substituents in positions 6′ and 8′ on sublimation enthalpy. The obtained results are the basis for the industrial application of these photochromic materials using vapor phase.