Multichromophore arrays of dibenzotetraaza[14]annulene: a promising platform for bioorganic chemistry

Zwoliński, Krzysztof; Eilmes, Julita

doi:10.1039/c8ob01078a

Cited by 4 publications

(2 citation statements)

References 75 publications

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“…As a result, the HOMO‐LUMO energy gap decreases by 0.063 eV. The most intense absorption band of both macrocycles are assigned to the π ‐ π * transition in the macrocylic DBTAA moiety, [ 44,45 ] whereas the weak absorption band at 339 nm of 6 is assigned to the π ‐ π * transition of the pyridoindolenine moiety. The calculated full‐half width maximum (FWHM) of 6 is broader than 5 , indicating a strong absorption of light with a wide wavelength range.…”

Section: Resultsmentioning

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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Section: Resultsmentioning

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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“…The ligand was then metallated with Zn(OAc)2 to generate 99 in high yield. The absorption spectrum of 98 shows two intense peaks at 345 and 386 nm, which corresponds to the π-π* and n-π*(imine) transitions of the macrocycle, respectively [90]. This synthetic approach offers strong fundamental prospects for the construction of DNA/RNA binders and as antiproliferative agents [12,13,83].…”

Section: Synthesis and Reactivity Of Meso-2-hydroxy-benzoyl-dbtaamentioning

confidence: 96%

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

Ramle

Tiekink

Basirun

2022

Coordination Chemistry Reviews

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Synthesis and Properties of Tris(3‐Pyrrolyl BODIPY) on 1, 3, 5‐Triazine Scaffold

Charan Behera,

Ravikanth

2024

Eur J Org Chem

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Tris(3‐pyrrolyl BODIPY) on 1,3,5‐triazine scaffold was synthesized over a sequence of steps starting from commercially available cyanuric chloride. The cyanuric chloride was reacted with p‐hydroxy benzaldehyde to afford 1,3,5‐triazine tris(p‐oxybenzaldehyde) which was then reacted with excess pyrrole under acid catalyzed conditions to afford 1,3,5‐triazine‐tris(meso‐p‐oxyphenyl dipyrromethane). Subsequent in situ oxidation of this compound with DDQ to obtain tris(meso‐oxyphenyldipyrromethene) which was then treated with pyrrole followed by the addition of Et3N/BF3⸱OEt2 afforded fluorescent tris(3‐pyrrolyl BODIPY). For comparison, tris(BODIPY) on the triazine scaffold was prepared by oxidizing tris(meso‐oxyphenyldipyrromethane) with DDQ followed by complexation with BF3⸱OEt2. Both compounds were thoroughly characterized and studied by various experimental and theoretical methods. Absorption, steady state fluorescence, time‐resolved fluorescence, and transient‐absorption studies revealed that in tris(3‐pyrrolyl BODIPY), excitonic interactions between two of the three 3‐pyrrolyl BODIPY units resulted in a hypsochromic shift in spectral bands, reducing the quantum yield and singlet state lifetime whereas tris(BODIPY) did not show such excitonic interactions. DFT studies helped in understanding the excitonic interactions in tris(3‐pyrrolyl BODIPY). The tris(3‐pyrrolyl BODIPY) was fluorescent both in solution and solid state. The viscosity studies indicated that the fluorescence of tris(3‐pyrrolyl BODIPY) increases significantly with solvent viscosity, suggesting its potential for measuring cellular viscosity during physiological processes.

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Multichromophore arrays of dibenzotetraaza[14]annulene: a promising platform for bioorganic chemistry

Cited by 4 publications

References 75 publications

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

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

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

Synthesis and Properties of Tris(3‐Pyrrolyl BODIPY) on 1, 3, 5‐Triazine Scaffold

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