White Light and Heat Sensitivity in a Pyridine-Based Polymer Blend

Vaganova, Evgenia; Wachtel, Ellen; Goldberg, Alex; Yitzchaik, Shlomo

doi:10.1021/jp3076063

Cited by 7 publications

(22 citation statements)

References 38 publications

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“…3 When P4VP is dissolved in dry liquid pyridine and allowed to gel, unique opto-and thermo-electronic behavior is observed. These properties have been studied extensively during the last few years, both experimentally [4][5][6] and by using computational methods. 7 Previously it was suggested that the unique optical properties of the P4VP gel are related to the transfer of a methyne proton to a side chain pyridine nitrogen with the formation of a pyridinium ion NH + .…”

mentioning

confidence: 99%

Acidity of the methyne group of poly(4-vinylpyridine) leads to side-chain protonation in pyridine

et al. 2015

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confidence: 99%

Acidity of the methyne group of poly(4-vinylpyridine) leads to side-chain protonation in pyridine

et al. 2015

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“…We demonstrate this concept on poly(4vinylpyridine) (PVPy)−pyridine (Py) smart gel optoelectronic devices. 41 This material proved to be useful in optoelectronics 53 and memory devices. 54 A PVPy−Py-derived device was fabricated from the smart gel as a photoactive material and assembled with modified ITO substrates.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…As predicted, the same trend of WF tuning was obtained for both ITO and Si/SiO 2 modification. Moreover, as a proof of concept, the modified ITO substrates were used in organic electronic devices. − The ability to control the WF of ITO improved the I – V performance of the modified ITO electrode-based device compared to the device built with bare ITO electrodes, thus proving the major role of monolayer modification on bulk and device features.…”

Section: Introductionmentioning

confidence: 99%

ITO Work Function Tunability by Polarizable Chromophore Monolayers

Gankin¹,

Mervinetsky²,

Alshanski³

et al. 2019

Langmuir

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The ability to tune the electronic properties of oxide-bearing semiconductors such as Si/SiO2 or transparent metal oxides such as indium-tin oxide (ITO) is of great importance in both electronic and optoelectronic device applications. In this work, we describe a process that was conducted on n-type Si/SiO2 and ITO to induce changes in the substrate work function (WF). The substrates were modified by a two-step synthesis comprising a covalent attachment of coupling agents’ monolayer followed by in situ anchoring reactions of polarizable chromophores. The coupling agents and chromophores were chosen with opposite dipole orientations, which enabled the tunability of the substrates’ WF. In the first step, two coupling agents with opposite molecular dipole were assembled. The coupling agent with a negative dipole induced a decrease in WF of modified substrates, while the coupling agent with a positive dipole produced an increase in WFs of both ITO and Si substrates. The second modification step consisted of in situ anchoring reaction of polarizable chromophores with opposite dipoles to the coupling layer. This modification led to an additional change in the WFs of both Si/SiO2 and ITO substrates. The WF was measured by contact potential difference and modeled by density functional theory-based theoretical calculations of the WF for each of the assembly steps. A good fit was obtained between the calculated and experimental trends. This ability to design and tune the WF of ITO substrates was implemented in an organic electronic device with improved I–V characteristics in comparison to a bare ITO-based device.

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“…Thoroughly dried P4VP dissolved in dry pyridine, taken in the equimolar ratio to the pyridine repeat units of the polymer, produces stable solid photo-and electrosensitive gels P4VP/Py [14]. The physical aggregation of polymer chains was shown to occur due to the presence of the hydrogen bond network, and these gels exhibit not only high ionic conductivity (polyelectrolyte behavior), but also enhanced photoinduced electron mobility [15,16]. The P4VP/Py gel was shown to exhibit unusual emission with the maxima at 477, 527, and 584 nm, explained by photoinduced proton transfer [17], which resembled the emission from the irradiated pyridine [12].…”

Section: Introductionmentioning

confidence: 99%

Light-Induced Reactions within Poly(4-vinyl pyridine)/Pyridine Gels: The 1,6-Polyazaacetylene Oligomers Formation

et al. 2021

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Cyclic 6-membered aromatic compounds such as benzene and azabenzenes (pyridine, pyridazine, and pyrazine) are known to be light-sensitive, affording, in particular, the Dewar benzene type of intermediates. Pyridine is known to provide the only Dewar pyridine intermediate that undergoes reversible ring-opening. We found that irradiation of photosensitive gels prepared from poly(4-vinyl pyridine) and pyridine at 254 or 312 nm leads to pyridine ring-opening and subsequent formation of 5-amino-2,4-pentadienals. We show that this light-induced process is only partially reversible, and that the photogenerated aminoaldehyde and aminoaldehyde-pending groups undergo self-condensation to produce cross-linked, conjugated oligomers that absorb light in the visible spectrum up to the near-infrared range. Such a sequence of chemical reactions results in the formation of gel with two distinct morphologies: spheres and fiber-like matrices. To gain deeper insight into this process, we prepared poly(4-vinyl pyridine) with low molecular weight (about 2000 g/mol) and monitored the respective changes in absorption, fluorescence, 1H-NMR spectra, and electrical conductivity. The conductivity of the polymer gel upon irradiation changes from ionic to electronic, indicative of a conjugated molecular wire behavior. Quantum mechanical calculations confirmed the feasibility of the proposed polycondensation process. This new polyacetylene analog has potential in thermal energy-harvesting and sensor applications.

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White Light and Heat Sensitivity in a Pyridine-Based Polymer Blend

Cited by 7 publications

References 38 publications

Acidity of the methyne group of poly(4-vinylpyridine) leads to side-chain protonation in pyridine

Acidity of the methyne group of poly(4-vinylpyridine) leads to side-chain protonation in pyridine

ITO Work Function Tunability by Polarizable Chromophore Monolayers

Light-Induced Reactions within Poly(4-vinyl pyridine)/Pyridine Gels: The 1,6-Polyazaacetylene Oligomers Formation

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