Studies on the Structure of <i>N</i>-Phenyl-Substituted Hexaaza[1<sub>6</sub>]paracyclophane: Synthesis, Electrochemical Properties, And Theoretical Calculation

Yang, Te‐Fang; Chiu, Kuo Yuan; Cheng, Hao; Lee, Yen Wei; Kuo, Ming Yu; Su, Yuhlong Oliver

doi:10.1021/jo301436g

Cited by 27 publications

(30 citation statements)

References 30 publications

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“…In the cyclic voltammogram of N6, CV patterns were similar to those of our previous results 22. Poor solubility affected the performance of the redox waves.…”

supporting

confidence: 86%

“…22 Wienk and Janssen conducted electrochemical studies of analogs, but the monomers (TPA) were linked at ortho and meta positions. 32 As the ortho and meta positions in a phenyl group are less interactive than the para position, well-resolved redox couples could be observed at the former two sites.…”

Section: Resultsmentioning

confidence: 99%

“…Although straight-chain compounds possessing the same or similar moieties (N1-N4 and N6) have been studied before, 2,22 we reinvestigated them to exploit their electronic properties systematically and in detail, and compared their electrochemical properties with those of N5. 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 Synthesis of N4.…”

Section: Introductionmentioning

confidence: 99%

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Linear Oligoarylamines: Electrochemical, EPR, and Computational Studies of Their Oxidative States

Cheng

Chiu

et al. 2015

J. Phys. Chem. A

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A series of straight-chain oligoarylamines were synthesized and examined by electrochemical, spectroelectrochemical, electron paramagnetic resonance techniques, and density functional theory (DFT) calculation. Depending on their electrochemical characteristics, these oligoarylamines were classified into two groups: one containing an odd number and the other an even number of redox centers. In the systems with odd redox centers (N1, N3, and N5), each oxidation was associated with the loss of one electron. As for the systems with even redox centers (N2, N4, and N6), oxidation occurred by taking N2 as a unit. Absorption spectra of linear oligoarylamines at various oxidative states were obtained to investigate their charge transfer behaviors. Moreover, DFT-computed isotropic hyperfine coupling constants and spin density were in accordance with the EPR experiment, and gave a close examination of oligoarylamines at charged states.

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“…In the cyclic voltammogram of N6, CV patterns were similar to those of our previous results 22. Poor solubility affected the performance of the redox waves.…”

supporting

confidence: 86%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Linear Oligoarylamines: Electrochemical, EPR, and Computational Studies of Their Oxidative States

Cheng

Chiu

et al. 2015

J. Phys. Chem. A

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“…According to literature, the second one-electron-oxidation of N,N,N',N'-tetraphenyl-p-phenylenediamine (TPPD) radical cation results in the rise of absorption at around 598 nm, indicating the generation of open-shelled diradical dication. [32] Given the similar behaviour of MC, the second oxidation step would involve concomitant two-electron removal from the diradical dication species to generate monoradical trication and closedshell tetracation species.…”

Section: Potentiostatic Uv-vis-nir Spectroelectrochemistrymentioning

confidence: 99%

Electrochemical and Spectroelectrochemical Comparative Study of Macrocyclic Thermally Activated Delayed Fluorescent Compounds: Molecular Charge Stability vs OLED EQE Roll‐Off

et al. 2020

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In this work, we present how a small change in molecular structure can affect the electrochemical stability of organic compounds. A new electron donor-acceptor-donoracceptor (D-AD A) macrocyclic π-conjugated compound (tBuMC) comprising of dibenzophenazine as As and N,N'-bis (t-butylphenyl)-p-phenylenediamines as Ds has been synthesized. The photophysical investigation uncovered that tBuMC showed thermally activated delayed fluorescence and that the organic light-emitting diodes (OLEDs) fabricated with tBuMC as the emitter achieved high external quantum efficiency (EQEs) of ca. 10%. However, the OLED with tBuMC showed a slightly lower EQE than that of the OLED with MC (11.6%) and showed greater EQE roll-off. Comparative studies on electrochemical properties of tBuMC, MC, and a linear analogue (Linear) revealed the introduction of t-Bu groups in the D-AD A scaffold causes a significant change in redox behavior. Full electrochemical and spectroelectrochemical studies gave clues to understand how the steric hindering group is affecting the charge distribution in the new molecules which results in a significant difference in the OLED roll-off. The electrochemical investigations together with UV-Vis-NIR and EPR analyses supported by quantum chemical theoretical calculations were performed, which provided us insights on the effect of structural modification on the redox properties of the D-AD A scaffold.

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“…The cyclohexameric amine, hexaaza [1 6 ]paracyclophane 51b (R = H) is not known, but several derivatives of it, in which some or all of the nitrogen atoms bear substituents, have been reported. [65][66][67] The sixfold cyclic ether 51c [cyclohexa(1,4-phenylene oxide)] was first described in 2006. 68 Applications of the compounds 51a-c in supramolecular chemistry have never been studied.…”

Section: Review Syn Thesis 5 Conclusionmentioning

confidence: 99%

Synthesis of Pillar[6]arenes and Their Host–Guest Complexes

Cao

Meier

2015

Synthesis

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Pillar[n]arenes are a fast-growing research topic in supramolecular chemistry. Originally the focus was predominantly on pillar[5]arenes; however, now more and more studies on pillar[6]arenes are being performed. The ability and selectivity of host-guest complexations depend strongly on the size of the inner cavities of these macrocycles. New results have stimulated us to compile the synthetic entries and the complexations of pillar[6]arenes with large cylindric cavities that offer space for many different guest molecules.

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Studies on the Structure of N-Phenyl-Substituted Hexaaza[1₆]paracyclophane: Synthesis, Electrochemical Properties, And Theoretical Calculation

Cited by 27 publications

References 30 publications

Linear Oligoarylamines: Electrochemical, EPR, and Computational Studies of Their Oxidative States

Linear Oligoarylamines: Electrochemical, EPR, and Computational Studies of Their Oxidative States

Electrochemical and Spectroelectrochemical Comparative Study of Macrocyclic Thermally Activated Delayed Fluorescent Compounds: Molecular Charge Stability vs OLED EQE Roll‐Off

Synthesis of Pillar[6]arenes and Their Host–Guest Complexes

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Studies on the Structure of N-Phenyl-Substituted Hexaaza[16]paracyclophane: Synthesis, Electrochemical Properties, And Theoretical Calculation

Cited by 27 publications

References 30 publications

Linear Oligoarylamines: Electrochemical, EPR, and Computational Studies of Their Oxidative States

Linear Oligoarylamines: Electrochemical, EPR, and Computational Studies of Their Oxidative States

Electrochemical and Spectroelectrochemical Comparative Study of Macrocyclic Thermally Activated Delayed Fluorescent Compounds: Molecular Charge Stability vs OLED EQE Roll‐Off

Synthesis of Pillar[6]arenes and Their Host–Guest Complexes

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Studies on the Structure of N-Phenyl-Substituted Hexaaza[1₆]paracyclophane: Synthesis, Electrochemical Properties, And Theoretical Calculation