New indole trimers as precursors for molecular electronic materials

Valentine, Robert A.; Whyte, Alexander M.; Awaga, Kunio; Robertson, Neil

doi:10.1016/j.tetlet.2011.11.124

Cited by 22 publications

(13 citation statements)

References 23 publications

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“…[32] Similar results were obtained by the Ruiz group; they showed that by lowering the symmetry of triindole, its photophysical and electronic properties can be tuned significantly, and also there is an improvement in fluorescence quantum yield. [33] Du et al showed that TN is rich in electronic character and electron delocalization than T. [34] Both the above-studied molecules T and TN are planar π-extended electron-rich molecules, which make these molecules have great potential application in DSSCs, [35] field-effect transistors (FETs), [36] OLEDs, [37,38] two-photon absorption (TPA), [39] and organic laser and fluorescent sensors. [33,40] Other analogs of T are oxatruxene (TO), silatruxene (TSi), and thiatruxene (TS), which are also synthesized, and their photophysical properties (except TS) are reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

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: Introductionmentioning

confidence: 99%

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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“…Our initial step was to find a convenient method for the trimerization of 1 H ‐indole‐6‐carboxylic acid ethyl ester (Scheme ). Trimerization of some substituted indoles has previously been reported . After modifying the reported conditions, Et 3 tat was successfully synthesized by the reaction of 1 H ‐indole‐6‐carboxylic acid ethyl ester with Br 2 in presence of excess formic acid.…”

Section: Resultsmentioning

confidence: 99%

“…Trimerization of some substituted indoles has previously been reported. [19] After modifying the reported conditions, Et 3 tat was successfully synthesized by the reaction of 1H-indole-6-carboxylic acid ethyl ester with Br 2 in presence of excess formic acid. The product was obtained directly by precipitation from the reactionm ixture in acceptable purity,a ss hown by 1 HNMR spectroscopy.T his compound was then hydrolyzed to obtain the parent triazatruxene ligand,H 3 tat.…”

Section: Resultsmentioning

confidence: 99%

Tritopic Triazatruxene Ligands for Multicomponent Metal‐Organic Frameworks

Alkaş

Cornelio

Telfer

2018

Chemistry An Asian Journal

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Multicomponent metal‐organic frameworks (MOFs) are built up from multiple ligands that are geometrically distinct. These ligands occupy specific positions in the MOF lattice. Installing different functionalities at precise locations in the framework is an important step in making MOFs for specific applications. This can be achieved by designing functionalized ligands for multicomponent MOFs. Here, we report a simple synthetic procedure for a new tritopic triazatruxene based tricarboxylic acid, H3tat. We show that this ligand can be symmetrically derivatized with various substituents on its nitrogen centres. We report a new isoreticular series of well‐ordered quaternary MOFs based on these new triazatruxene ligands together with two linear carboxylate ligands and Zn4O clusters. These MOFs are isostructural to the previously reported MUF‐77 series and show similar high surface areas and large pore volumes. Furthermore, H‐bonding between the NH sites of the incorporated triazatruxene ligands and guest molecules is employed to modify their fluorescence behavior.

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“…Some TATs can behave as twophoton absorption chromophores, [8] can generate electroactive discotic liquid crystals, [9] and have been tested in organic fieldeffect transistors (OFETs). [10] Reported applications of TATs include the development of bulk heterojunction solar cells, [11] organic light-emitting diodes (OLEDs), [12] and sensing devices. [13] In this paper we report: the synthesis, separation, and comparative characterization of eumelanin-inspired symmetric and asymmetric TATs prepared from 5,6-dimethoxyindole (1 a and 2 a), 5,6-dibenzyloxyindole (1 b,c and 2 b,c), and 6-hydroxyindole (1 d and 2 d); a detailed characterization of their optoelectronic properties with the support of quantum chemical calculations based on TD-DFT; preliminary evidence of self-assembly behavior in solution; the applications of these TATs as emitting materials in OLED devices.…”

Section: Introductionmentioning

confidence: 99%

Melanin‐Inspired Organic Electronics: Electroluminescence in Asymmetric Triazatruxenes

et al. 2015

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The oxidative polymerization of 5,6‐dihydroxyindoles and related hydroxyindoles at pH<3 is diverted from the usual eumelanin‐forming pathway to produce mixtures of symmetric and asymmetric triazatruxenes (TATs), which could be separated and characterized for their opto‐electronic properties with the aid of TD‐DFT calculations. Data showed that the asymmetric isomers exhibit higher fluorescence quantum efficiencies, lower HOMO–LUMO gaps, better film homogeneity, and a more definite aggregation behavior than the symmetric counterparts, suggesting promising applications in organic electronics. The enhanced luminance exhibited by the OLED devices fabricated with blends of the synthesized TATs in poly‐9‐vinylcarbazole confirmed the potential of the asymmetric skeleton as new versatile platform for light‐emitting materials.

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New indole trimers as precursors for molecular electronic materials

Abstract: We thank the University of Edinburgh for funding and the EPSRC and JST for support of the UK-Japan collaboration.

Cited by 22 publications

References 23 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

Tritopic Triazatruxene Ligands for Multicomponent Metal‐Organic Frameworks

Melanin‐Inspired Organic Electronics: Electroluminescence in Asymmetric Triazatruxenes

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