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. |
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| 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] |
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| Database: | Engineering Source |
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| 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] |
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| ISSN: | 20734360 |
| DOI: | 10.3390/polym17101316 |
