Unconventional polymerization of thiophene siloxane oligomers. Optoelectronic behavior and computational calculations

Jean Medina; Patricio A. Sobarzo; René A. Hauyon; Luis E. Garcia; Enzo B. González; Eduardo Schott; Ignacio A. Jessop; Carmen M. González-Henríquez; Ximena Zarate; César Saldías; Alain Tundidor-Camba; Claudio A. Terraza

doi:10.1016/j.eurpolymj.2025.113830

Unconventional polymerization of thiophene siloxane oligomers. Optoelectronic behavior and computational calculations

Jean Medina
, Patricio A. Sobarzo
, René A. Hauyon
, Luis E. Garcia
, Enzo B. González
, Eduardo Schott
, Ignacio A. Jessop
, Carmen M. González-Henríquez
, Ximena Zarate
, César Saldías
, Alain Tundidor-Camba
, Claudio A. Terraza

Department of Chemistry

Pontificia Universidad Católica de Chile
Universidad Tecnológica Metropolitana
Instituto Universitario de Investigación y Desarrollo Tecnológico (IDT)
Universidad Autónoma de Chile
University of Alabama

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

Four novel siloxane-functionalized oligo(azomethine)s (o-AzThs) containing thiophene and alkyl-thiophene units were successfully synthesized via a high-temperature polycondensation reaction between dichlorodiphenylsilane and four diphenol monomers incorporating imine linkages. The resulting o-AzThs were characterized by spectroscopic methods (NMR, FTIR) and elemental analysis. These oligomers, composed for 4–9 repeating units per chain exhibited excellent solubility in common aprotic polar solvents, moderate molecular weights (M_n = 2.94–4.70 kDa), and narrow polydispersity indices (PDI ≈ 1.1). The new o-AzThs displayed thermal stability up to 223–370 °C and glass transition temperatures ranging from 56 to 91 °C. Optoelectronic analysis showed a broad absorption–emission behavior with bandgaps values of 2.36–2.52 eV, along with low HOMO energy levels (−5.24 to −5.36 eV) suggesting their potential applications in optoelectronic field.

Original language	English
Article number	113830
Journal	European Polymer Journal
Volume	228
DOIs	https://doi.org/10.1016/j.eurpolymj.2025.113830
State	Published - 19 Mar 2025

Keywords

Computational calculations
Diphenylsiloxane
Oligo(azomethine)
Thiophene
Wide-bandgap donor

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10.1016/j.eurpolymj.2025.113830

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Medina, J., Sobarzo, P. A., Hauyon, R. A., Garcia, L. E., González, E. B., Schott, E., Jessop, I. A., González-Henríquez, C. M., Zarate, X., Saldías, C., Tundidor-Camba, A., & Terraza, C. A. (2025). Unconventional polymerization of thiophene siloxane oligomers. Optoelectronic behavior and computational calculations. European Polymer Journal, 228, Article 113830. https://doi.org/10.1016/j.eurpolymj.2025.113830

@article{6d62fbc06ae144f1a74edc28ba087696,

title = "Unconventional polymerization of thiophene siloxane oligomers. Optoelectronic behavior and computational calculations",

abstract = "Four novel siloxane-functionalized oligo(azomethine)s (o-AzThs) containing thiophene and alkyl-thiophene units were successfully synthesized via a high-temperature polycondensation reaction between dichlorodiphenylsilane and four diphenol monomers incorporating imine linkages. The resulting o-AzThs were characterized by spectroscopic methods (NMR, FTIR) and elemental analysis. These oligomers, composed for 4{\textendash}9 repeating units per chain exhibited excellent solubility in common aprotic polar solvents, moderate molecular weights (Mn = 2.94{\textendash}4.70 kDa), and narrow polydispersity indices (PDI ≈ 1.1). The new o-AzThs displayed thermal stability up to 223{\textendash}370 °C and glass transition temperatures ranging from 56 to 91 °C. Optoelectronic analysis showed a broad absorption{\textendash}emission behavior with bandgaps values of 2.36{\textendash}2.52 eV, along with low HOMO energy levels (−5.24 to −5.36 eV) suggesting their potential applications in optoelectronic field.",

keywords = "Computational calculations, Diphenylsiloxane, Oligo(azomethine), Thiophene, Wide-bandgap donor",

author = "Jean Medina and Sobarzo, \{Patricio A.\} and Hauyon, \{Ren{\'e} A.\} and Garcia, \{Luis E.\} and Gonz{\'a}lez, \{Enzo B.\} and Eduardo Schott and Jessop, \{Ignacio A.\} and Gonz{\'a}lez-Henr{\'i}quez, \{Carmen M.\} and Ximena Zarate and C{\'e}sar Sald{\'i}as and Alain Tundidor-Camba and Terraza, \{Claudio A.\}",

note = "Publisher Copyright: {\textcopyright} 2025 Elsevier Ltd",

year = "2025",

month = mar,

day = "19",

doi = "10.1016/j.eurpolymj.2025.113830",

language = "English",

volume = "228",

journal = "European Polymer Journal",

issn = "0014-3057",

}

Medina, J, Sobarzo, PA, Hauyon, RA, Garcia, LE, González, EB, Schott, E, Jessop, IA, González-Henríquez, CM, Zarate, X, Saldías, C, Tundidor-Camba, A & Terraza, CA 2025, 'Unconventional polymerization of thiophene siloxane oligomers. Optoelectronic behavior and computational calculations', European Polymer Journal, vol. 228, 113830. https://doi.org/10.1016/j.eurpolymj.2025.113830

TY - JOUR

T1 - Unconventional polymerization of thiophene siloxane oligomers. Optoelectronic behavior and computational calculations

AU - Medina, Jean

AU - Sobarzo, Patricio A.

AU - Hauyon, René A.

AU - Garcia, Luis E.

AU - González, Enzo B.

AU - Schott, Eduardo

AU - Jessop, Ignacio A.

AU - González-Henríquez, Carmen M.

AU - Zarate, Ximena

AU - Saldías, César

AU - Tundidor-Camba, Alain

AU - Terraza, Claudio A.

PY - 2025/3/19

Y1 - 2025/3/19

N2 - Four novel siloxane-functionalized oligo(azomethine)s (o-AzThs) containing thiophene and alkyl-thiophene units were successfully synthesized via a high-temperature polycondensation reaction between dichlorodiphenylsilane and four diphenol monomers incorporating imine linkages. The resulting o-AzThs were characterized by spectroscopic methods (NMR, FTIR) and elemental analysis. These oligomers, composed for 4–9 repeating units per chain exhibited excellent solubility in common aprotic polar solvents, moderate molecular weights (Mn = 2.94–4.70 kDa), and narrow polydispersity indices (PDI ≈ 1.1). The new o-AzThs displayed thermal stability up to 223–370 °C and glass transition temperatures ranging from 56 to 91 °C. Optoelectronic analysis showed a broad absorption–emission behavior with bandgaps values of 2.36–2.52 eV, along with low HOMO energy levels (−5.24 to −5.36 eV) suggesting their potential applications in optoelectronic field.

AB - Four novel siloxane-functionalized oligo(azomethine)s (o-AzThs) containing thiophene and alkyl-thiophene units were successfully synthesized via a high-temperature polycondensation reaction between dichlorodiphenylsilane and four diphenol monomers incorporating imine linkages. The resulting o-AzThs were characterized by spectroscopic methods (NMR, FTIR) and elemental analysis. These oligomers, composed for 4–9 repeating units per chain exhibited excellent solubility in common aprotic polar solvents, moderate molecular weights (Mn = 2.94–4.70 kDa), and narrow polydispersity indices (PDI ≈ 1.1). The new o-AzThs displayed thermal stability up to 223–370 °C and glass transition temperatures ranging from 56 to 91 °C. Optoelectronic analysis showed a broad absorption–emission behavior with bandgaps values of 2.36–2.52 eV, along with low HOMO energy levels (−5.24 to −5.36 eV) suggesting their potential applications in optoelectronic field.

KW - Computational calculations

KW - Diphenylsiloxane

KW - Oligo(azomethine)

KW - Thiophene

KW - Wide-bandgap donor

UR - https://www.scopus.com/pages/publications/85217943327

U2 - 10.1016/j.eurpolymj.2025.113830

DO - 10.1016/j.eurpolymj.2025.113830

M3 - Article

AN - SCOPUS:85217943327

SN - 0014-3057

VL - 228

JO - European Polymer Journal

JF - European Polymer Journal

M1 - 113830

ER -

Unconventional polymerization of thiophene siloxane oligomers. Optoelectronic behavior and computational calculations

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Keywords

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