Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges

Karaman, C.; Goker, Seza; Hacıoğlu, Şerife O.; Hacıefendioǧlu, Tuǧba; Yıldırım, Erol; Toppare, Levent

doi:10.1149/1945-7111/abedc5

Cited by 8 publications

(5 citation statements)

References 46 publications

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“…The predicted quinoid characters were comparable to earlier reports on CA-RE products [11,19]. Inspired by the literature on strong D-A systems [49,50] these results were further confirmed by total average atomic charges (δ) by ESP fitting on donor, acceptor and PAH parts of push-pull chromophores. Atomic charges were calculated based on the ESP fitting scheme of Merz-Singh-Kollman (MK) [51].…”

Section: Theoretical Studiessupporting

confidence: 87%

Polycyclic aromatic hydrocarbon-substituted push–pull chromophores: an investigation of optoelectronic and nonlinear optical properties using experimental and theoretical approaches

Dengiz¹

2021

Turk J Chem

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IntroductionDonor-π-acceptor (D-π-A)-type push-pull chromophores, are well-known for their desirable features, such as tunable strong intramolecular charge-transfer bands that absorb light in a wide range of area including visible and near-IR regions, spectacular nonlinear optical properties, excellent solubility, and high thermal stabilities [1][2][3]. With these desired properties, push-pull chromophores have already been employed in a series of advanced applications such as photovoltaics, [4,5] light-emitting diodes, [6,7] sensors, [1,8,9] and NLO devices [1,10,11]. The successful integration of push-pull systems in high technology areas makes it necessary to design and synthesize new molecular structures with enhanced optoelectronic properties. However, synthetic strategies to access these entities are arguably limited and require multi-step protocols. The formal [2+2] cycloaddition-retroelectrocyclization (CA-RE) is one of the promising reaction candidates to circumvent these synthetic problems [1]. With its high-yielding nature and broad substrate scope, [2+2] CA-RE transformation occurs under very mild conditions without requiring a catalyst and fulfills all the requirements to be referred as a "click-type reaction" [12,13] [2+2] CA-RE transformation requires electron-rich alkynes and electrondeficient alkenes to synthesize nonplanar D-π-A systems [1]. Bruce and co-workers reported the first example of [2+2] CA-RE reactions between ruthenium-substituted acetylides and tetracyanoethylene (TCNE) in 1981 [14]. Later, metalfree substrates have also been employed in CA-RE reactions for the synthesis of structurally demanding push-pull chromophores by Diederich and co-workers [11]. The short and easy-to-perform CA-RE method has increased the variety in the design of the target push-pull chromophores. When the structures of push-pull chromophores obtained by CA-RE reactions are examined in detail, derivatization is mostly made in two main parts (donor groups and acceptor groups).

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Section: Theoretical Studiessupporting

confidence: 87%

Polycyclic aromatic hydrocarbon-substituted push–pull chromophores: an investigation of optoelectronic and nonlinear optical properties using experimental and theoretical approaches

Dengiz¹

2021

Turk J Chem

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“…Compounds 2-5 were synthesized following typical synthetic conditions reported for analogous compounds in the literature. [45][46][47] The Sonogashira coupling of dibromo dihexyloxy benzothiadiazole (5) with TIPS acetylene, followed by the reduction of thiadiazole resulted in the phenylene diamine compound 7. Nucleophilic aromatic substitution reaction (S N Ar) by 7 onto 2,3-dichloro-5,6dicyanopyrazine in 1,4-dioxane gave dihydrotetraazacenedicyano compound 8.…”

Section: Synthesis Of Monomersmentioning

confidence: 99%

Pyrazinacene conjugated polymers: a breakthrough in synthesis and unraveling the conjugation continuum

Hameed,

Maity,

Francis

et al. 2024

Chem. Sci.

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“…Theoretical calculations were performed by using Gaussian09 (A02 software package) . Density functional theory (DFT) methods were applied for the tetramers, in the form of (D–B–A–B) 4 (D, donor; A, acceptor; B, bridge) at B3LYP hybrid functional with 6-311g(d) basis set with tight SCF convergence criteria which have presented successful results in previous studies. − Geometry optimizations were started from different initial conformations such as the relative conformation of donor and acceptor by controlling the torsional angle between connected donor, acceptor, and bridge units, as shown in Figure S1 systemically to determine the lowest energy geometries. Electrostatic potential surface (ESP), highest occupied molecular orbitals (HOMO), and lowest unoccupied molecular orbitals (LUMO) were calculated for the optimized geometries of tetramers.…”

Section: Theoretical Calculationsmentioning

confidence: 99%

Design Principles for the Acceptor Units in Donor–Acceptor Conjugated Polymers

Hacıefendioǧlu

Yıldırım

2022

ACS Omega

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More than 50 different acceptor units from the experimental literature have been modeled, analyzed, and compared by using the computationally extracted data from the density functional theory (DFT) perspective for tetramer structures in the form of (D−B−A−B) 4 (D, donor; A, acceptor; B, bridge) with fixed donor and bridge units. Comparison of dihedral angle between acceptor, donor, and bridge units, bond order, and hyperpolarizability reveals that these three structural properties have a dominant effect on the frontier electronic energy levels of the acceptor units. Systematic investigation of the structural properties has demonstrated the band gap energy dependency of the acceptor units on the planarity, conjugation, and the electron delocalization. Substitution effect, morphological alternation, and insertion of π-electron deficient atoms in A unit have also an important role to determine physical properties of the donor−acceptor conjugated polymers. This benchmark study will be beneficial for the band gap engineering and molecular design of the donor−acceptor copolymers using different acceptor units for the organic electronic applications.

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Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges

Cited by 8 publications

References 46 publications

Polycyclic aromatic hydrocarbon-substituted push–pull chromophores: an investigation of optoelectronic and nonlinear optical properties using experimental and theoretical approaches

Polycyclic aromatic hydrocarbon-substituted push–pull chromophores: an investigation of optoelectronic and nonlinear optical properties using experimental and theoretical approaches

Pyrazinacene conjugated polymers: a breakthrough in synthesis and unraveling the conjugation continuum

Design Principles for the Acceptor Units in Donor–Acceptor Conjugated Polymers

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