Indolenine – dibenzotetraaza [14] annulene Ni (II) complexes as sensitizers for dye - sensitized solar cells

Ramle, Abdul Qaiyum; Khaledi, Hamid; Hashim, Ameerul Hazeeq; Mingsukang, M. A.; Arof, A. K.; Ali, Hapipah Mohd; Basirun, Wan Jefrey

doi:10.1016/j.dyepig.2019.01.009

Cited by 15 publications

(10 citation statements)

References 44 publications

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“…However, no emission peaks were observed for 61, 62 and 68 relative to H260 due to the energy loss by non-radiative decay [70]. A similar methodology was also described by Ramle et al [3,73] who diversified and extended the π-conjugation system of indoleninyl-DBTAA framework (Figure 13).…”

Section: Synthesis and Reactivity Of Meso-pyridyl Dbtaasupporting

confidence: 53%

“…Dibenzotetraaza [14]annulenes (DBTAAs) are a class of macrocyclic compounds that have attracted a great deal of attention mainly due to their being an attractive structural model for naturally-occurring porphyrin derivatives [1,2]. The unique features of DBTAA give rise to a wide scope of applications such as in dye-sensitized solar cells [3], catalase mimics [4,5], field-effect transistors [6], as electrical conductors [7,8], corrosion inhibitors [9], sensors [10],…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, functionalization and coordination chemistry of dibenzotetraaza[14]annulenes

Ramle

Tiekink

Basirun

2022

Coordination Chemistry Reviews

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Section: Synthesis and Reactivity Of Meso-pyridyl Dbtaasupporting

confidence: 53%

Section: Introductionmentioning

confidence: 99%

Synthesis, functionalization and coordination chemistry of dibenzotetraaza[14]annulenes

Ramle

Tiekink

Basirun

2022

Coordination Chemistry Reviews

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“…[ 9,10 ] Besides, the DBTAA is easily synthesized by a simple [2 + 2] Schiff base condensation reaction between a 1, 3‐dicarbonyl and o ‐phenylene diamine reactants. [ 11 ] However, changing the substituent at the meso ‐position of the DBTAA molecule is quite challenging due to the limited synthetic possibilities.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic and theoretical optical properties of indoleninyl‐substituted dibenzotetraaza[14]annulenes

Ramle

Karakas

Arof

et al. 2020

Journal of Heterocyclic Chem

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Two new macrocyclic dibenzotetraaza[14]annulene (DBTAA) compounds with indolenine (5) and pyridoindolenine (6) moieties were synthesized and characterized by spectroscopy. Both DBTAAs exhibit strong UV-Vis absorption properties in the Soret band region. The theoretical second-order nonlinear optical property, electric dipole moment (μ), dispersion-free dipole polarizability (α) and first hyper-polarizability values were calculated by density functional theory and time dependent density functional theory. The ab-initio quantum mechanical calculation by time-dependent Hartree-Fock method was utilized to investigate the dynamic dipole polarizabilities, dynamic second-order, static, and dynamic third-order (γ) hyper-polarizabilities of the DBTAAs. The configuration interaction technique of all doubly occupied molecular orbitals possesses theoretically defined single-photon absorption (OPA) specifications for the examined structures. The computed maximum OPA wavelengths on both macrocyclic compounds coincide with the preceding measurement outcomes.

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“…Being synthetic analogues of naturally occurring porphyrins, tetraaza[14]annulenes are a class of well-known synthetic macrocycles. − The four nitrogen atoms of tetraaza[14]annulenes can be easily deprotonated to generate dianionic ligands that coordinate with metal ions to form metal tetraaza[14]annulenes. , Metal tetraaza[14]annulenes have been applied in catalase mimics, field effect transistors, catalysts, and dye-sensitized solar cells. − Marks et al reported that a partial oxidation of the ligand in Ni(II) tetraaza[14]annulene by iodine led to the formation of an electrically conductive metallo-macrocycle . However, metal tetraaza[14]annulenes have not been used so far to produce framework materials, although attaching this macrocycle to a framework material could be promising for many applications.…”

Section: Introductionmentioning

confidence: 99%

Partial Oxidation-Induced Electrical Conductivity and Paramagnetism in a Ni(II) Tetraaza[14]annulene-Linked Metal Organic Framework

Jiang

Joo

et al. 2019

J. Am. Chem. Soc.

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We report the synthesis and characterization of a two-dimensional (2D) conjugated Ni(II) tetraaza[14]annulene-linked metal organic framework (NiTAA-MOF) where NiTAA is a macrocyclic MN4 (M = metal, N = nitrogen) compound. The structure of NiTAA-MOF was elucidated by Fourier-transform infrared, X-ray photoemission, and X-ray diffraction spectroscopies, in combination with density functional theory (DFT) calculations. When chemically oxidized by iodine, the insulating bulk NiTAA-MOF (σ < 10–10 S/cm) exhibits an electrical conductivity of 0.01 S/cm at 300 K, demonstrating the vital role of ligand oxidation in the electrical conductivity of 2D MOFs. Magnetization measurements show that iodine-doped NiTAA-MOF is paramagnetic with weak antiferromagnetic coupling due to the presence of organic radicals of oxidized ligands and high-spin Ni(II) sites of the missing-linker defects. In addition to providing further insights into the origin of the induced electrical conductivity in 2D MOFs, both pristine and iodine-doped NiTAA-MOF synthesized in this work could find potential applications in areas such as catalase mimics, catalysis, energy storage, and dynamic nuclear polarization-nuclear magnetic resonance (DNP-NMR).

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Indolenine – dibenzotetraaza [14] annulene Ni (II) complexes as sensitizers for dye - sensitized solar cells

Cited by 15 publications

References 44 publications

Synthesis, functionalization and coordination chemistry of dibenzotetraaza[14]annulenes

Synthesis, functionalization and coordination chemistry of dibenzotetraaza[14]annulenes

Spectroscopic and theoretical optical properties of indoleninyl‐substituted dibenzotetraaza[14]annulenes

Partial Oxidation-Induced Electrical Conductivity and Paramagnetism in a Ni(II) Tetraaza[14]annulene-Linked Metal Organic Framework

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