Octupolar (C3 and S4) Symmetric Cyclized Indole Derivatives: Syntheses, Structures, and NLO Properties

Wang, Lei; Fang, Qi; Lü, Qing; Zhang, Shaojun; Jin, Yingying; Liu, Zhi Qiang

doi:10.1021/acs.orglett.5b01912

Cited by 31 publications

(28 citation statements)

References 52 publications

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“…The experimentally reported absorption maximum for T is 273 nm, while its asymmetrical isomer IT is giving an intense peak at 337 nm . For the isomers TN and ITN , intense absorption peak were observed at 309 and 345 nm, respectively . These experimental results suggest that asymmetric isomers are always red‐shifted than their corresponding symmetric isomers.…”

Section: Resultsmentioning

confidence: 71%

Optoelectronic and charge‐transport properties of truxene, isotruxene, and its heteroatomic (N, O, Si, and S) analogs: A DFT study

Tripathi

Chetti

2019

J of Physical Organic Chem

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The main objective of this work is to provide a detailed study of optoelectronic and charge‐transport properties of truxene, isotruxene, and their heteroatomic analogs (azatruxene and isoazatruxene, oxatruxene and isooxatruxene, silatruxene and isosilatruxene, and thiatruxene and isothiatruxene). Systematic studies of these molecules were performed by means of the density functional theory (DFT) and time‐dependent DFT (TD‐DFT) calculations. Electronic excitations (absorption spectra), reorganization energies (hole‐ and electron‐transport properties), electron affinities (EAs), ionization potentials (IPs), hole extraction potentials (HEPs), and electron extraction potentials (EEPs) for all the molecules were reported. Based on the comparative study, it is showed that thiatruxenes (isothiatruxene) are better hole‐transport materials than other truxene (isotruxene) analogs.

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Section: Resultsmentioning

confidence: 71%

Optoelectronic and charge‐transport properties of truxene, isotruxene, and its heteroatomic (N, O, Si, and S) analogs: A DFT study

Tripathi

Chetti

2019

J of Physical Organic Chem

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“…Most recently, cyclic tetraindole analogue TTI fused with four indole units has also been successfully synthesized, showing interesting electron‐donating characters because of their electron‐rich multi‐indole structures . Recent studies prove its promising potential applications in non‐linear optics and dye‐sensitized solar cells . Based on the studies, it is surmised that constructing large π‐extended PAHs systems fused with multiple indole scaffolds is rather attractive for optoelectronic applications because of their electron‐rich features.…”

Section: Figurementioning

confidence: 99%

Unexpected One‐Pot Synthesis of Diindolotriazatruxene: A Planar Electron‐Rich Scaffold Toward Highly π‐Extended PAHs

Wang

Xue

et al. 2017

Asian J Org Chem

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Au niquep lanar and highly p-extended scaffold, 3,8,14,, was synthesized via af acile one-pots trategy.T he structure of 4Br-DIT was adequately verified by MALDI-TOFm ass spectrometry, 1 Ha nd 13 CNMR, and single-crystal XRD analysis. Ac ombination of thermal, optical, and electrochemical investigation confirmed the electron-richc haracteristics of the resulting diindolotriazatruxene unit, showingp romise as ab uilding block to construct highly p-extended polycyclic aromatic hydrocarbons (PAHs).

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“…The five-membered ringtype cross-linked derivatives, such as truxene, have been studied for their non-linear optical and semiconductor properties. Interestingly, numerous derivatives, in which the bridged carbon atom of truxene was converted into spiro carbon, [3] carbonyl, [4] nitrogen, [5] oxygen, [6] sulfur, [7] and phosphorus, [8] have been reported. Conversely, the six-membered ring-type derivatives linked by ethylene, [9] ether, [10] and vinylene units [11] have been synthesized, and their photochemical properties have been investigated.…”

Section: Introductionmentioning

confidence: 99%

Triskelion‐Shaped π‐Luminophores Bearing Coumarin: Syntheses, Structures, and Luminescence Properties

2020

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Triskelion-shaped π-luminophores bearing three coumarin units 1 a and 1 b were successfully synthesized by the intramolecular Ullmann coupling reaction of triphenyl benzene-1,3,5-tricarboxylate derivatives. X-ray crystal structure analysis revealed that compound 1 adopts a unique curved and three-blade propeller-shaped structure. These crystals are a racemic mixture consisting of PPP-and MMM-1 due to the helicity resulting from the steric hindrance. A computational study suggests that this helical inversion process between PPP-and MMM-1 a occurs with comparative ease. The emission spectra of 1 a and 1 b in THF solution showed sharp emission bands at 454 nm and 492 nm, respectively. The Stokes shifts were relatively large at 7385 cm À 1 and 6556 cm À 1 due to their degenerate frontier molecular orbitals. A solution of 1 b in different organic solvents demonstrated solvatofluorochromism due to intramolecular charge transfer of the coumarin unit in the excited states. Interestingly, both triskelion-shaped molecules formed aggregates in a mixture of THF-H 2 O and exhibited aggregationinduced emission enhancement characteristics.

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Octupolar (C₃ and S₄) Symmetric Cyclized Indole Derivatives: Syntheses, Structures, and NLO Properties

Cited by 31 publications

References 52 publications

Optoelectronic and charge‐transport properties of truxene, isotruxene, and its heteroatomic (N, O, Si, and S) analogs: A DFT study

Optoelectronic and charge‐transport properties of truxene, isotruxene, and its heteroatomic (N, O, Si, and S) analogs: A DFT study

Unexpected One‐Pot Synthesis of Diindolotriazatruxene: A Planar Electron‐Rich Scaffold Toward Highly π‐Extended PAHs

Triskelion‐Shaped π‐Luminophores Bearing Coumarin: Syntheses, Structures, and Luminescence Properties

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