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Silicon-Containing π-Conjugated Schiff Base Oligomers with Naphthalene or Binaphthalene Moieties in the Backbone: Synthesis and Study of Properties.

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Title: Silicon-Containing π-Conjugated Schiff Base Oligomers with Naphthalene or Binaphthalene Moieties in the Backbone: Synthesis and Study of Properties.
Authors: González, Enzo1 (AUTHOR), González, Alexis F.2 (AUTHOR), Mariman, Andrea P.2,3 (AUTHOR), Jara, Camilo I.3,4 (AUTHOR), Velázquez, Joel D.3,5 (AUTHOR), Saldías, César2,6 (AUTHOR), Schott, Eduardo4,7 (AUTHOR), Zarate, Ximena1,5 (AUTHOR), Tundidor-Camba, Alain2,6 (AUTHOR), Sobarzo, Patricio A.3,7 (AUTHOR), Terraza, Claudio A.1,4 (AUTHOR)
Source: Polymers (20734360). May2025, Vol. 17 Issue 10, p1316. 18p.
Subjects: Schiff bases, Core materials, Visible spectra, Thermal resistance, Stokes shift
Abstract: Four silane-containing Schiff base oligomers (o-SBNs and o-SBBs) were synthesized by high-temperature polycondensation reactions using silicon-based dialdehydes with naphthalene and 1,1'-binaphthalene diamine derivates. The samples showed a moderate solubility in common organic solvents, where the incorporation of TPS cores into o-SBN2 allows the formation of highly soluble material in non-polar solvents with higher molecular weights (11.58 kDa) and polydispersity. All oligo-SBs displayed high thermal resistance (above 450 °C), showing enhanced thermal stability for TPS-containing oligomers, with the degradation temperature exceeding 530 °C (o-SBB2) and high Tg values due to the higher aromatic content granted by TPS and 1,1'-binaphthalene moieties. Optical results of the oligo-SBs showed broad absorption and emission behavior in the visible spectrum, ranging from deep blue (o-SBN1 and o-SBB1) to blue (o-SBN2 and o-SBB2). The structure promotes a clear bathochromic shift for TPS-based oligomers, attributed to an extended π-conjugation across the backbone. In addition, the π-π overlap effect highlights larger Stokes shifts for the DMS core oligomers o-SN2 (133 nm) and o-SBB1 (195 nm). The oligo-SBs were found to be wide-bandgap materials, with Egopt values in the range of 2.60 eV to 3.67 eV. The higher molecular weight of o-SBN2, which provided an extended π-conjugation, allows the lowest value of Egopt (2.60 eV) to be achieved. In addition, DFT, TDDFT and EDDM calculations were performed on trimeric oligo-SBs, revealing that HOMOs are localized in the amine-terminal fraction, while LUMOs are localized over the terminal aldehyde groups. These findings highlight the used DMS and TPS cores in Schiff base materials, providing valuable insights into fine-tuning physicochemical properties through the use of suitable building blocks and their potential as optoelectronic materials. [ABSTRACT FROM AUTHOR]
Copyright of Polymers (20734360) is the property of MDPI and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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  Data: Silicon-Containing π-Conjugated Schiff Base Oligomers with Naphthalene or Binaphthalene Moieties in the Backbone: Synthesis and Study of Properties.
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  Data: <searchLink fieldCode="AR" term="%22González%2C+Enzo%22">González, Enzo</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22González%2C+Alexis+F%2E%22">González, Alexis F.</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Mariman%2C+Andrea+P%2E%22">Mariman, Andrea P.</searchLink><relatesTo>2,3</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Jara%2C+Camilo+I%2E%22">Jara, Camilo I.</searchLink><relatesTo>3,4</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Velázquez%2C+Joel+D%2E%22">Velázquez, Joel D.</searchLink><relatesTo>3,5</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Saldías%2C+César%22">Saldías, César</searchLink><relatesTo>2,6</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Schott%2C+Eduardo%22">Schott, Eduardo</searchLink><relatesTo>4,7</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Zarate%2C+Ximena%22">Zarate, Ximena</searchLink><relatesTo>1,5</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Tundidor-Camba%2C+Alain%22">Tundidor-Camba, Alain</searchLink><relatesTo>2,6</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Sobarzo%2C+Patricio+A%2E%22">Sobarzo, Patricio A.</searchLink><relatesTo>3,7</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Terraza%2C+Claudio+A%2E%22">Terraza, Claudio A.</searchLink><relatesTo>1,4</relatesTo> (AUTHOR)
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  Data: <searchLink fieldCode="JN" term="%22Polymers+%2820734360%29%22">Polymers (20734360)</searchLink>. May2025, Vol. 17 Issue 10, p1316. 18p.
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  Data: <searchLink fieldCode="DE" term="%22Schiff+bases%22">Schiff bases</searchLink><br /><searchLink fieldCode="DE" term="%22Core+materials%22">Core materials</searchLink><br /><searchLink fieldCode="DE" term="%22Visible+spectra%22">Visible spectra</searchLink><br /><searchLink fieldCode="DE" term="%22Thermal+resistance%22">Thermal resistance</searchLink><br /><searchLink fieldCode="DE" term="%22Stokes+shift%22">Stokes shift</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: Four silane-containing Schiff base oligomers (o-SBNs and o-SBBs) were synthesized by high-temperature polycondensation reactions using silicon-based dialdehydes with naphthalene and 1,1'-binaphthalene diamine derivates. The samples showed a moderate solubility in common organic solvents, where the incorporation of TPS cores into o-SBN2 allows the formation of highly soluble material in non-polar solvents with higher molecular weights (11.58 kDa) and polydispersity. All oligo-SBs displayed high thermal resistance (above 450 °C), showing enhanced thermal stability for TPS-containing oligomers, with the degradation temperature exceeding 530 °C (o-SBB2) and high Tg values due to the higher aromatic content granted by TPS and 1,1'-binaphthalene moieties. Optical results of the oligo-SBs showed broad absorption and emission behavior in the visible spectrum, ranging from deep blue (o-SBN1 and o-SBB1) to blue (o-SBN2 and o-SBB2). The structure promotes a clear bathochromic shift for TPS-based oligomers, attributed to an extended π-conjugation across the backbone. In addition, the π-π overlap effect highlights larger Stokes shifts for the DMS core oligomers o-SN2 (133 nm) and o-SBB1 (195 nm). The oligo-SBs were found to be wide-bandgap materials, with Egopt values in the range of 2.60 eV to 3.67 eV. The higher molecular weight of o-SBN2, which provided an extended π-conjugation, allows the lowest value of Egopt (2.60 eV) to be achieved. In addition, DFT, TDDFT and EDDM calculations were performed on trimeric oligo-SBs, revealing that HOMOs are localized in the amine-terminal fraction, while LUMOs are localized over the terminal aldehyde groups. These findings highlight the used DMS and TPS cores in Schiff base materials, providing valuable insights into fine-tuning physicochemical properties through the use of suitable building blocks and their potential as optoelectronic materials. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
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  Data: <i>Copyright of Polymers (20734360) is the property of MDPI and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.3390/polym17101316
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        Text: English
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      – SubjectFull: Visible spectra
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              Text: May2025
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