53348-05-3Relevant articles and documents
Dynamic extension-contraction motion in supramolecular springs
Kim, Ho-Joong,Lee, Eunji,Park, Hye-Seo,Lee, Myongsoo
, p. 10994 - 10995 (2007)
We have prepared coordination polymers with bent conformations that adopt a helical structure with reversible extension-contraction motions, triggered by temperature. Furthermore, this dynamic conformational change leads to a fluorescence switching between the fluorescent stretched and nonfluorescent compressed states of the supramolecular springs. Copyright
Blue-orange emitting carbazole based donor-acceptor derivatives: Synthesis and studies of modulating acceptor unit on opto-electrochemical and theoretical properties
Badani, Purav M.,Kamble, Rajesh M.,Singh, Pooja S.
, (2021)
In order to demonstrate an effect of varying acceptor unit on optoelectronic properties of Donor–Acceptor (D–A) assembly, we herein designed and synthesized C–N coupled, carbazole based dyes 1–8 by employing Buchwald–Hartwig coupling amination reaction and fully characterized by spectroscopic methods. Presence of intramolecular charge transfer (ICT) transitions (λmax = 403–467 nm) in absorption spectra of all dyes reminiscent D–A assembly in it and emit in blue–yellow region (λemm = 467–565 nm) in solution state with marked positive solvatochromism. The photophysical studies of some of the dyes in different THF/water mixtures revealed aggregation-induced emission (AIE) feature with the nanoparticles formation, as confirmed by dynamic light scattering (DLS) technique. The HOMO (?5.42 to ?5.74 eV) and LUMO (?3.03 to ?3.50 eV) energy level of these molecules measured by cyclic voltammetry suggest electron transporting property in it. Further, DFT/TDDFT calculation of dyes, indicate quite comparable theoretical and experimental photophysical and electrochemical data. Moreover, calculated singlet (S1) and triplet (T1) excitation energy levels by DFT/B3LYP/6–311 G+(d,p) shows small ΔEST value for some dyes and hence called as TADF emitters. Thus obtained all optoelectrochemical properties of dyes propose its potential use in optoelectronic devices and in biosensing.
Synthesis and investigation of the photophysical, electrochemical and theoretical properties of phenazine-Amine based cyan blue-red fluorescent materials for organic electronics
Chacko, Sajeev,Kanekar, Deepali N.,Kamble, Rajesh M.
, p. 3278 - 3293 (2020)
To understand the structure-property relationship, we have designed and synthesized seven novel donor-Acceptor based phenazine-Amines, 2-8, by the Buchwald-Hartwig coupling amination reaction in moderate yield. The synthesized molecules were fully characterized and the influence of modulating the donor and phenazine core on the optoelectrochemical properties was studied. The absorption spectra of 2-8 display intramolecular charge transfer (ICT) transitions in the range of 431-501 nm. Dyes 2-8 exhibit positive solvatofluorochromism and emit in the cyan blue-red region with emission maxima at 498-641 nm on excitation at their respective ICT maxima in toluene, chloroform, DCM and neat solid film. The photophysical studies of the dyes in different THF/water mixtures revealed aggregation induced emission (AIE) features in dyes 2, 3 and 5. The HOMO and LUMO energy levels were found to be in the ranges of-5.39 to-5.68 eV and-3.59 to-3.71 eV, respectively, with electrochemical band gaps within the range 1.73-2.04 eV. Theoretical studies of the molecules were also carried out by using TD-DFT calculations. The comparable electrochemical energy levels to ambipolar materials, solid state luminescence with AIE characteristics and good thermal stability of the synthesized dyes signify their potential to be used as solid state emitters and ambipolar materials in optoelectronics.
Novel electroluminescent donor-acceptors based on dibenzo[a,c]phenazine as hole-transporting materials for organic electronics
Shaikh, Azam M.,Sharma, Bharat K.,Chacko, Sajeev,Kamble, Rajesh M.
, p. 628 - 638 (2017)
A series of novel donor-acceptor type of molecules (2-6) based on dibenzo[a,c]phenazine were synthesized by employing a palladium = catalyzed C-N bond forming amination reaction in a good yield and were then fully characterized, whereby the optical properties of 2-6 were determined by UV-vis absorption, fluorescence spectroscopy, and the electrochemical properties by cyclic voltammetry. The absorption spectra of 2-6 showed intramolecular charge transfer (ICT) transitions in the range of 447-513 nm in solution. The HOMO and LUMO energy levels of 2-6 were in the range from ?5.03 to ?5.29 eV and ?2.75 to ?2.87 eV, respectively, with an electrochemical band gap within 2.26-2.45 eV. The HOMO energy levels of 2-6 are comparable with those of the most commonly used hole-transporting materials, which makes them potential candidates for hole-transporting materials in organic electronics.
Study of modulating opto-electrochemical properties in Suzuki coupled phenazine derivatives for organic electronics
Kanekar, Deepali N.,Badani, Purav M.,Kamble, Rajesh M.
, p. 5945 - 5961 (2021)
In this work, five 3,6,11-trisubstituted-dibenzo[a,c]phenazine (2–6) derivatives were synthesized by employing Palladium-catalyzed Suzuki–Miyaura ‘C–C bond’ coupling reaction and characterized. Absorption spectra of 2–6 show the formation of charge-transfer complexes. Dyes exhibit blue-green fluorescence with emission maxima 434–506?nm in various solvents and neat solid film. To elucidate AIE phenomenon, photophysical properties of dye 2 and 3 in different THF/water mixture were studied. The HOMO and LUMO energy level were found in the range of ? 6.38 to ? 6.82?eV and ? 3.67 to ? 3.75?eV with an electrochemical bandgap of 2.71–3.08?eV. The HOMO and LUMO distribution in molecules were further studied by DFT/TD–DFT calculations. Herein, characteristic blue emission, comparable energy levels with n-type materials, and good thermal stability of derivatives make them a potential candidate for their application in optoelectronics. Graphic abstract: [Figure not available: see fulltext.].
Highly fluorescent blue-green emitting phenanthroimidazole derivatives: Detail experimental and DFT study of structural and donating group effects on fluorescence properties
Kothavale, Shantaram,Bhalekar, Sulochana,Sekar, Nagaiyan
, p. 209 - 221 (2018)
A series of highly fluorescent blue-green emitting phenanthrene and 3,6-diphenylphenanthrene based compounds have been synthesized to study the effect of different electron donating groups on photophysical properties. A very unique and different fluorescence properties are observed in the case of N-phenyl carbazole donor based compounds as compared to the other electron donating groups. Observed intramolecular charge transfer and highly polar excited states of these compounds are elucidated by Lipert-Mataga correlations. The positive and negative solvatochromism observed from non-polar to polar solvents is also supported using Kamlet-Taft and Catalan multilinear regression analysis. Comparative study of photophysical properties between benzil, phenanthrene and 3,6-diphenylphenanthrene based hydroxyl imidazole derivatives is presented to study the effect of rigidity and extended conjugation. Observed experimental results are also correlated theoretically using Density Functional theory computations.
Geometric Complementarity in Assembly and Guest Recognition of a Bent Heteroleptic cis-[Pd2 L A2 L B2] Coordination Cage
Bloch, Witold M.,Abe, Yoko,Holstein, Julian J.,Wandtke, Claudia M.,Dittrich, Birger,Clever, Guido H.
, p. 13750 - 13755 (2016)
Due to the inherent difficulties in achieving a defined and exclusive formation of multicomponent assemblies against entropic predisposition, we present the rational assembly of a heteroleptic [Pd2LA2LB2]4+ coordination cage achieved through the geometric complementarity of two carefully designed ligands, LA and LB. With Pd(II) cations as rigid nodes, the pure distinctly angular components readily form homoleptic cages, a [Pd2LA4]4+ strained helical assembly and a [Pd4LB8]8+ box-like structure, both of which were characterized by X-ray analysis. Combined, however, the two ligands could be used to cleanly assemble a cis-[Pd2LA2LB2]4+ cage with a bent architecture. The same self-sorted product was also obtained by a quantitative cage-to-cage transformation upon mixing of the two homoleptic cages revealing the [Pd2LA2LB2]4+ assembly as the thermodynamic minimum. The structure of the heteroleptic cage was examined by ESI-MS, COSY, DOSY, and NOESY methods, the latter of which pointed toward a cis-conformation of ligands in the assembly. Indeed, DFT calculations revealed that the angular ligands and strict Pd(II) geometry strongly favor the cis-[Pd2LA2LB2]4+ species. The robust nature of the cis-[Pd2LA2LB2]4+ cage allowed us to probe the accessibility of its cavity, which could be utilized for shape recognition toward stereoisomeric guests. The ability to directly combine two different backbones in a controlled manner provides a powerful strategy for increasing complexity in the family of [Pd2L4] cages and opens up possibilities of introducing multiple functionalities into a single self-assembled architecture.
On-Surface Synthesis and Characterization of a Cycloarene: C108 Graphene Ring
Fan, Qitang,Martin-Jimenez, Daniel,Werner, Simon,Ebeling, Daniel,Koehler, Tabea,Vollgraff, Tobias,Sundermeyer, J?rg,Hieringer, Wolfgang,Schirmeisen, André,Gottfried, J. Michael
, p. 894 - 899 (2020)
The synthesis of cycloarenes in solution is challenging because of their low solubility and the often hindered cyclodehydrogenation reaction of their nonplanar precursors. Using an alternative on-surface synthesis protocol, we achieved an unprecedented double-stranded hexagonal cycloarene containing 108 sp2 carbon atoms. Its synthesis is based on hierarchical Ullmann coupling and cyclodehydrogenation of a specially designed precursor on a Au(111) surface. The structure and other properties of the cycloarene are investigated by scanning tunneling microscopy/spectroscopy, atomic force microscopy, and density functional theory calculations.
Rechargeable Aluminum Organic Batteries
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Paragraph 0102; 0103, (2021/08/06)
Disclosed herein are rechargeable aluminum organic batteries and active materials used therein. The cathodic materials used herein comprise a macrocycle comprising a substituted or unsubstituted phenanthrenequinone unit and a graphite flake.
Regioisomers of Organic Semiconducting Dumbbell-Shaped Molecules: Synthesis and Structure-Properties Relationship
Bulut, Ibrahim,Fall, Sadiara,Heinrich, Beno?t,Heiser, Thomas,Jing, Jiang,Lévêque, Patrick,Leclerc, Nicolas,Méry, Stéphane,Mahmoudi, Chaima,Majdoub, Mustapha,Steveler, Emilie
supporting information, p. 3170 - 3177 (2021/06/28)
Two new dumbbell-shaped molecules based on two solubilizing and structuring triazatruxene (TAT) units linked by a central chromophore were synthesized and studied. The central chromophore was an electro-deficient fluorene-malononitrile (FM) unit, that can be functionalized symmetrically on two different positions, giving rise to two positional isomers, called TAT-pFM and TAT-mFM, when the TATs are connected to the 2,7- and 3,6-positions, respectively. The two isomers exhibited different electronic conjugation pathways that drastically affect their absorption properties and energy levels. Moreover, while TAT-pFM was organized in a stable 3D mesomorphic structure from room-temperature to the melting point, TAT-mFM remained crystalline and decomposed before melting. Finally, despite a lower hole mobility, the TAT-mFM exhibited the highest Power Conversion Efficiency (PCE) of about 2 % in organic solar cells. This higher PCE was attributed essentially to the pronounced internal charge transfer band contribution to the charge photogeneration observed in TAT-mFM solar cells.
