Synthesis of phosphate and silane-based conjugated polymers derived from bis-azomethine: Photophysical and thermal characterization

Çulhaoğlu, Süleyman; Kolcu, Feyza; Kaya, İsmet

doi:10.1016/j.reactfunctpolym.2021.104978

Cited by 7 publications

(5 citation statements)

References 63 publications

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“…As shown in Figure A, the proton signals observed at 9.73 and 8.54 ppm were attributed to the -O H and - H CN- functional groups of SCH-1, respectively. Similarly, for SCH-2, these proton signals were detected at 9.55 ppm and 8.41 ppm (see Figure S1A), in accordance with values reported in the literature . The presence of a peak assigned to the H CN group in the spectrum confirmed the formation of the SCHs.…”

Section: Resultssupporting

confidence: 89%

“…As shown in Figure , the vibrational band values for the imine (HCN) bond of compounds SCH-1, P1–P, P1–Si, SCH-2, P2–P, and P2–Si were observed at 1611, 1620, 1620, 1612, 1609, and 1614 cm –1 , respectively. This observation provided compelling evidence of imine (HCN) bond formation in the synthesized compounds, indicating that the azomethine groups remained intact during oligomerization . The upshift observed in the CN vibration frequencies within the oligomers may be attributed to the integration of dichlorodiethylsilane and dichlorophosphate groups, resulting in the formation of polar Si–O and P–O bonds.…”

Section: Resultsmentioning

confidence: 76%

“…Similarly, for SCH-2, these proton signals were detected at 9.55 ppm and 8.41 ppm (see Figure S1A ), in accordance with values reported in the literature. 62 The presence of a peak assigned to the H C=N group in the spectrum confirmed the formation of the SCHs. The ratio of two protons of the - H C=N– group to two aromatic –OH protons being 1 provided evidence of symmetry in the structure of SCH-1.…”

Section: Resultsmentioning

confidence: 87%

“…This observation provided compelling evidence of imine (HC=N) bond formation in the synthesized compounds, indicating that the azomethine groups remained intact during oligomerization. 62 The upshift observed in the C=N vibration frequencies within the oligomers may be attributed to the integration of dichlorodiethylsilane and dichlorophosphate groups, resulting in the formation of polar Si–O and P–O bonds. The confirmation of phenyl dichlorophosphate attachment to SCH-1 and SCH-2 was subsequently ascertained by the observation of P=O vibrational bands, which exhibited overlap with the Schiff base structural moieties.…”

Section: Resultsmentioning

confidence: 96%

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Comparative Study of Bis-Schiff Case Containing Conjugated Oligomers Based on Phosphate and Silane Moieties: Investigation of Photophysical and Thermal Properties

Kolcu,

Çulhaoğlu,

Kaya

2024

ACS Omega

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Oligo(azomethine)s bearing phosphate and silane moieties were the subject of an investigation within this study. The initial stage involved the synthesis of two Schiff base monomers, denoted as SCH-1 and SCH-2 (SCHs), each possessing a pair of hydroxyl functional groups. This was achieved through a loss of water between the aldehyde and diamine precursors. Subsequently, the Schiff base entities were subjected to oligomerization through HCl-mediated elimination due to the interaction between the hydroxyl groups of the Schiff bases and the chlorine moieties of dichlorodiethylsilane (Si) or phenyl dichlorophosphate (P). This procedure yielded distinct P-oligo(azomethine) (P1−P, P2−P) and Si-oligo(azomethine) (P1−Si and P2−Si) structures corresponding to each precursor. The molecular structures of the synthesized Schiff base monomers and oligo(azomethine)s were elucidated employing Fourier transform infrared, 1 H NMR, and 13 C NMR techniques. Thermal properties of the resulting products were assessed by utilizing thermogravimetric analysis (TG-DTG/ DTA and DSC) techniques. Scanning electron microscopy (SEM) was employed to acquire high-resolution images and detailed surface information on the samples. Additionally, X-ray diffraction was employed to analyze the phase properties of the solid samples. Furthermore, the optical band gap (E g ) values of the resulting P-oligo(azomethine)s and Si-oligo(azomethine)s were determined utilizing UV−vis spectrophotometer. The relatively low band gap values exhibited by the synthesized oligo(azomethine)s were indicative of their potential suitability as semiconductive materials in the realm of electronic and optoelectronic device fabrication. Photoluminescence (PL) measurements disclosed a green emission profile upon excitation by blue light. The oligo(azomethine)s incorporating methoxy groups demonstrated a red shift in comparison to their counterparts with methyl groups. Remarkably, no discernible fluctuations in fluorescence were observed over a 3600 s interval under consistent conditions. This observation underscored the inherent stability of the PL emission across the spectral range of exciting light. Thermal analyses unveiled high thermal stability of the synthesized oligo(azomethine)s, sustaining their structural integrity up to 220 °C. The char % of P-oligo(azomethine)s and Si-oligo(azomethine)s were observed to fall within the range of 29.45−55.47% at 1000 °C. SEM images revealed the absence of pores on the surface of P2−Si, which exhibited the highest limiting oxygen index and thermal heat release index (T HRI ) values.

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Section: Resultssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 76%

Section: Resultsmentioning

confidence: 87%

Section: Resultsmentioning

confidence: 96%

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Comparative Study of Bis-Schiff Case Containing Conjugated Oligomers Based on Phosphate and Silane Moieties: Investigation of Photophysical and Thermal Properties

Kolcu,

Çulhaoğlu,

Kaya

2024

ACS Omega

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“…Silanes are monomeric chemicals capable of bonding organic resins to inorganic materials such as glass, mineral fillers, metals and metallic oxides. The readily available d-orbitals, which are available for silanes enhanced reactivity when compared to its analogue methane, which can be attributed to the increased reactivity of silane (1)(2)(3).…”

Section: Introductionmentioning

confidence: 99%

Chemistry and Applications of Organosilanes – An Overview

Indumathy¹,

Gunasekhar²,

Sathiyanathan³

et al. 2022

ECS Trans.

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Organofunctional silanes are hybrid materials of silanes having attracted greater attention since the last decade owing to its versatile properties and wide range of applications. In this review, we have summarized the types of organosilanes (RnSiX4-n), their reactions, and applications. Organosilanes usually have two reactive groups, organofunctional groups and hydrolyzable alkoxy groups, which undergo hydrolysis and condensation. Silanols (Si-OH) and siloxane (Si-O-Si) structures are formed by hydrolysis and condensation reactions, respectively. In general, organosilanes acts as excellent binding agent due to its bridging capacity through (Si-O-Si) bond linkage with metal surfaces. From the extensive literature survey carried out, we understand that the silanes are synthesized without comprehending the reaction kinetics mechanism. In the past few decades, significant advances were witnessed in the development of various organofunctional silanes, which were used in a wide range of research areas based on its bifunctional characteristics.

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Fluorinated Oligoazomethine with Azo Groups in the Main Chain as Stimuli-Responsive Photoactive Materials

Kurioz

Ткаченко

Kovalchuk

et al. 2023

Springer Proceedings in Physics

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Synthesis of phosphate and silane-based conjugated polymers derived from bis-azomethine: Photophysical and thermal characterization

Cited by 7 publications

References 63 publications

Comparative Study of Bis-Schiff Case Containing Conjugated Oligomers Based on Phosphate and Silane Moieties: Investigation of Photophysical and Thermal Properties

Comparative Study of Bis-Schiff Case Containing Conjugated Oligomers Based on Phosphate and Silane Moieties: Investigation of Photophysical and Thermal Properties

Chemistry and Applications of Organosilanes – An Overview

Fluorinated Oligoazomethine with Azo Groups in the Main Chain as Stimuli-Responsive Photoactive Materials

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