Synthesis of D-π-A′-π-A Chromophores with Quinoxaline Core as Auxiliary Acceptor and Effect of Various Silicon-Substituted Donor Moieties on Thermal and Nonlinear Optical Properties at Molecular and Material Level
Novel D-π-A′-π-A chromophores with quinoxaline cores as auxiliary acceptors and various donor moieties (aniline, carbazole, phenothiazine, tetrahydroquinoline) containing bulky <i>tert</i>-butyldimethylsilyloxy (TBDMSO) groups and tricyanofuranyl (TCF) acceptors with bulky cyclohexylphen...
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2023-01-01
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| author | Alexey A. Kalinin Liliya N. Islamova Sirina M. Sharipova Guzel M. Fazleeva Alexey A. Shustikov Adel I. Gaysin Artemiy G. Shmelev Anastasiya V. Sharipova Tatyana A. Vakhonina Olga D. Fominykh Olga B. Babaeva Ayrat R. Khamatgalimov Marina Yu. Balakina |
| author_facet | Alexey A. Kalinin Liliya N. Islamova Sirina M. Sharipova Guzel M. Fazleeva Alexey A. Shustikov Adel I. Gaysin Artemiy G. Shmelev Anastasiya V. Sharipova Tatyana A. Vakhonina Olga D. Fominykh Olga B. Babaeva Ayrat R. Khamatgalimov Marina Yu. Balakina |
| author_sort | Alexey A. Kalinin |
| collection | DOAJ |
| description | Novel D-π-A′-π-A chromophores with quinoxaline cores as auxiliary acceptors and various donor moieties (aniline, carbazole, phenothiazine, tetrahydroquinoline) containing bulky <i>tert</i>-butyldimethylsilyloxy (TBDMSO) groups and tricyanofuranyl (TCF) acceptors with bulky cyclohexylphenyl substituents were synthesized via eight- to nine-step procedures, and their photo-physical and thermal properties were investigated. The values of the chromophores’ first hyperpolarizabilities were calculated in the framework of DFT at the M06-2X/aug-cc-pVDZ computational level; the effect of the introduction of the TBDMSO group into the donor fragment is shown to be inessential, as this group is not coupled to the π-conjugated system of the chromophore. The chromophore with the tetrahydroquinoline donor has a first hyperpolarizability value of 937 × 10<sup>−30</sup> esu, which is the highest for the studied chromophores. Atomistic modeling of composite materials with the studied chromophores as guests demonstrated that the presence of bulky substituent in the donor fragment prevents notable aggregation of chromophores, even at high chromophore content (40 wt.%). The nonlinear optical performance of guest–host materials with 25 and 40 wt.% of suggested chromophore content was studied using a second harmonic generation technique to give the NLO coefficient, <i>d</i><sub>33</sub> up to 52 pm/V. |
| first_indexed | 2024-03-09T11:36:58Z |
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| id | doaj.art-652e897368eb4df7a45d3f1168662c7e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T11:36:58Z |
| publishDate | 2023-01-01 |
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| series | Molecules |
| spelling | doaj.art-652e897368eb4df7a45d3f1168662c7e2023-11-30T23:41:10ZengMDPI AGMolecules1420-30492023-01-0128253110.3390/molecules28020531Synthesis of D-π-A′-π-A Chromophores with Quinoxaline Core as Auxiliary Acceptor and Effect of Various Silicon-Substituted Donor Moieties on Thermal and Nonlinear Optical Properties at Molecular and Material LevelAlexey A. Kalinin0Liliya N. Islamova1Sirina M. Sharipova2Guzel M. Fazleeva3Alexey A. Shustikov4Adel I. Gaysin5Artemiy G. Shmelev6Anastasiya V. Sharipova7Tatyana A. Vakhonina8Olga D. Fominykh9Olga B. Babaeva10Ayrat R. Khamatgalimov11Marina Yu. Balakina12Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, RussiaNovel D-π-A′-π-A chromophores with quinoxaline cores as auxiliary acceptors and various donor moieties (aniline, carbazole, phenothiazine, tetrahydroquinoline) containing bulky <i>tert</i>-butyldimethylsilyloxy (TBDMSO) groups and tricyanofuranyl (TCF) acceptors with bulky cyclohexylphenyl substituents were synthesized via eight- to nine-step procedures, and their photo-physical and thermal properties were investigated. The values of the chromophores’ first hyperpolarizabilities were calculated in the framework of DFT at the M06-2X/aug-cc-pVDZ computational level; the effect of the introduction of the TBDMSO group into the donor fragment is shown to be inessential, as this group is not coupled to the π-conjugated system of the chromophore. The chromophore with the tetrahydroquinoline donor has a first hyperpolarizability value of 937 × 10<sup>−30</sup> esu, which is the highest for the studied chromophores. Atomistic modeling of composite materials with the studied chromophores as guests demonstrated that the presence of bulky substituent in the donor fragment prevents notable aggregation of chromophores, even at high chromophore content (40 wt.%). The nonlinear optical performance of guest–host materials with 25 and 40 wt.% of suggested chromophore content was studied using a second harmonic generation technique to give the NLO coefficient, <i>d</i><sub>33</sub> up to 52 pm/V.https://www.mdpi.com/1420-3049/28/2/531D-π-A′-π-A chromophoresquinoxalinesilicon-substituted donorNLO activitysecond harmonic generation |
| spellingShingle | Alexey A. Kalinin Liliya N. Islamova Sirina M. Sharipova Guzel M. Fazleeva Alexey A. Shustikov Adel I. Gaysin Artemiy G. Shmelev Anastasiya V. Sharipova Tatyana A. Vakhonina Olga D. Fominykh Olga B. Babaeva Ayrat R. Khamatgalimov Marina Yu. Balakina Synthesis of D-π-A′-π-A Chromophores with Quinoxaline Core as Auxiliary Acceptor and Effect of Various Silicon-Substituted Donor Moieties on Thermal and Nonlinear Optical Properties at Molecular and Material Level Molecules D-π-A′-π-A chromophores quinoxaline silicon-substituted donor NLO activity second harmonic generation |
| title | Synthesis of D-π-A′-π-A Chromophores with Quinoxaline Core as Auxiliary Acceptor and Effect of Various Silicon-Substituted Donor Moieties on Thermal and Nonlinear Optical Properties at Molecular and Material Level |
| title_full | Synthesis of D-π-A′-π-A Chromophores with Quinoxaline Core as Auxiliary Acceptor and Effect of Various Silicon-Substituted Donor Moieties on Thermal and Nonlinear Optical Properties at Molecular and Material Level |
| title_fullStr | Synthesis of D-π-A′-π-A Chromophores with Quinoxaline Core as Auxiliary Acceptor and Effect of Various Silicon-Substituted Donor Moieties on Thermal and Nonlinear Optical Properties at Molecular and Material Level |
| title_full_unstemmed | Synthesis of D-π-A′-π-A Chromophores with Quinoxaline Core as Auxiliary Acceptor and Effect of Various Silicon-Substituted Donor Moieties on Thermal and Nonlinear Optical Properties at Molecular and Material Level |
| title_short | Synthesis of D-π-A′-π-A Chromophores with Quinoxaline Core as Auxiliary Acceptor and Effect of Various Silicon-Substituted Donor Moieties on Thermal and Nonlinear Optical Properties at Molecular and Material Level |
| title_sort | synthesis of d π a π a chromophores with quinoxaline core as auxiliary acceptor and effect of various silicon substituted donor moieties on thermal and nonlinear optical properties at molecular and material level |
| topic | D-π-A′-π-A chromophores quinoxaline silicon-substituted donor NLO activity second harmonic generation |
| url | https://www.mdpi.com/1420-3049/28/2/531 |
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