TY - JOUR
T1 - Pyrene-based chalcones as functional materials for organic electronics application
AU - Kagatikar, Sneha
AU - Sunil, Dhanya
AU - Kekuda, Dhananjaya
AU - Satyanarayana, M. N.
AU - Kulkarni, Suresh D.
AU - Sudhakar, Y. N.
AU - Vatti, Anoop Kishore
AU - Sadhanala, Aditya
N1 - Funding Information:
The advancements in organic electronics such as photovoltaics, field-effect transistors, and OLEDs have recently shown an increased interest and demand in suitable π-functional materials [14]. Dipolar chromophores, which are composed of electron donor (D) and electron acceptor (A) groups linked by a conjugated π-bridge, are currently being actively explored and used in optoelectronic and electronic devices [15,16]. Pyrene is a widely explored fluorophoric system with strong π-electron delocalization that exhibits good thermal and emission properties [13]. The pyrene unit is substantively planar, and adjacent pyrene rings are linked by aromatic π-π stacking interactions in the crystal packing [17]. In the present study, two chalcones having a D–π–A architecture with pyrene as electron donor linked to phenyl (in PC1) and fluorophenyl (in PC2) as acceptors via an enone moiety as a π-bridge have been synthesized. The intrinsic features; thermal, electrochemical, electrical, and optical of both the pyrene-based chalcones have been investigated. Systematic DFT calculations and molecular dynamic simulation (MDS) studies are used to support the intramolecular charge transfer (ICT) and AIEE properties of the two chalcones observed experimentally.The CV curve (Fig. 10E) exhibited an almost rectangular shape in all scan rates with a small peak at 0.55 V in the positive sweep curve. This behavior is more of double electric layer capacitance with little contribution from fluorine atom. The Nyquist plot of the supercapacitor as portrayed in Fig. 10F was fitted into an equivalent circuit, which consisted of R1, R2, W, and Q, and exhibited a small semicircle in the higher frequency region and linear response in the lower frequency region. Charge transfer resistance, which includes both electronic and ionic resistances was obtained as Rct (0.2091 Ω), and solution resistance was 0.040 Ω. Analogous to the CV results, the AC impedance studies supported the diffusion process with little charge transfer between PC2 and electrode surface [42]. Hence, PC2 can be a suitable candidate for enhancing the specific capacitance of the supercapacitor, and provides an opportunity for further studies.
Publisher Copyright:
© 2022 Elsevier B.V.
PY - 2023/1/1
Y1 - 2023/1/1
N2 - Though new generation organic electronic devices have evolved from mere scientific perceptions to real-life marketed applications, considerably less research attention has been focused on n-type or electron transporting small molecule semiconductors. The present study is focused on the exploration of structural, thermal, electrochemical, electrical, and optical properties of two pyrene-based chalcones: PC1 and PC2, synthesized through Claisen Schmidt condensation reaction. The chalcones displayed good thermal stability and wide bandgap n-type semiconducting behaviour with high charge carrier concentration and dielectric constant. The experimental evidences including fluorescence measurements, nanoaggregate size, and morphology analysis, supported by DFT calculations and molecular dynamic simulations advocated the intramolecular charge transfer and aggregation-induced enhanced emission features of the molecules. Successful fabrication of a diode in combination with the current-voltage characteristics established the candidature of PC1 and PC2 for electro-optical devices. The dielectric studies were performed to measure dielectric constant and AC conductivity at different frequency ranges. The cyclic voltammetry and AC impedance response of PC2 differed from PC1 due to the inclusion of a fluorine atom in the molecular scaffold. Further, the functional implication of PC2 as an electrode material was explored by constructing a supercapacitor, which offered a specific capacitance of 220 Fg-1 at a scan rate of 10 mV s−1. Moreover, these chalcone-based organic semiconductors displayed high thermal and charge carrier concentration as well as compatibility with other layers in an OLED device. Hence PC1/PC2 can be further investigated as dopants along with other emissive layers as host materials in OLEDs.
AB - Though new generation organic electronic devices have evolved from mere scientific perceptions to real-life marketed applications, considerably less research attention has been focused on n-type or electron transporting small molecule semiconductors. The present study is focused on the exploration of structural, thermal, electrochemical, electrical, and optical properties of two pyrene-based chalcones: PC1 and PC2, synthesized through Claisen Schmidt condensation reaction. The chalcones displayed good thermal stability and wide bandgap n-type semiconducting behaviour with high charge carrier concentration and dielectric constant. The experimental evidences including fluorescence measurements, nanoaggregate size, and morphology analysis, supported by DFT calculations and molecular dynamic simulations advocated the intramolecular charge transfer and aggregation-induced enhanced emission features of the molecules. Successful fabrication of a diode in combination with the current-voltage characteristics established the candidature of PC1 and PC2 for electro-optical devices. The dielectric studies were performed to measure dielectric constant and AC conductivity at different frequency ranges. The cyclic voltammetry and AC impedance response of PC2 differed from PC1 due to the inclusion of a fluorine atom in the molecular scaffold. Further, the functional implication of PC2 as an electrode material was explored by constructing a supercapacitor, which offered a specific capacitance of 220 Fg-1 at a scan rate of 10 mV s−1. Moreover, these chalcone-based organic semiconductors displayed high thermal and charge carrier concentration as well as compatibility with other layers in an OLED device. Hence PC1/PC2 can be further investigated as dopants along with other emissive layers as host materials in OLEDs.
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U2 - 10.1016/j.matchemphys.2022.126839
DO - 10.1016/j.matchemphys.2022.126839
M3 - Article
AN - SCOPUS:85140135559
SN - 0254-0584
VL - 293
JO - Materials Chemistry and Physics
JF - Materials Chemistry and Physics
M1 - 126839
ER -