Self-Assembly of <i>C</i><sub>3</sub>-Symmetrical Hexaaryltriindoles Driven by Solvophobic and CH−π Interactions

García-Frutos, Eva M.; Hennrich, Gunther; Gutiérrez, Enrique; Monge, Ángeles; Gómez‐Lor, Berta

doi:10.1021/jo902013v

Cited by 41 publications

(35 citation statements)

References 49 publications

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“…5,6 A study of the electronic character of the peripheral substituents on their selfassociation behavior indicates that contrary to what is commonly observed, increasing the electron-donating character of the terminal substituents, facilitates self-association while electron-withdrawing groups inhibite aggregation. A study of the self-assembly process at different solvent compositions shows that upon the stacking tendency increases with the polarity of the solvent.…”

Section: Structure-supramolecular Organization Relationshipsmentioning

confidence: 97%

New triindole-based organic semiconductors: structure-property relationships

et al. 2010

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We introduce a new family of stable high-mobility organic π-type semiconductors based on the electron-rich 10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole (triindole) extended π-conjugated system. This platform tends to form columnar stacks of the aromatic cores maximizing π-orbital overlap between adjacent molecules, thus paving the way for the one-dimensional migration of charge carriers along the columns. In addition these compounds have two different types of positions that can be functionalized independently offering the possibility of tuning their electronic properties as well as their morphology through chemical functionalization. The integration of the optimized triindole derivatives into solution processed devices as active layer is explored in this work.

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Section: Structure-supramolecular Organization Relationshipsmentioning

confidence: 97%

New triindole-based organic semiconductors: structure-property relationships

et al. 2010

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“…This technique revealed upfield chemical shifts of the aromatic signals with increasing concentration, suggesting solvophobic-induced aromatic interactions. [20] Significant concentration-dependent effects were observed for the asymmetric 2 d and to a minor extent for the symmetrical 1 a, indicating that the lack of symmetry in the TAT backbone not only does not impair p-p stacking but, conversely, drives more efficient aggregating interactions (Figure 4). …”

Section: Opto-electronic Properties and Self-assembly Behavior Of Melmentioning

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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“…is unlikely to be significantly different from monomers. [ 30,31 ] Further experiments are needed to clarify this point. In summary, these measurements clearly demonstrate the effects of solvent quality, oxygen solubility, near-neighbour interactions and aggregation on the photostability of acenes in solution.…”

Section: Concentration-and Solvent-dependent Photochemical Instabilitmentioning

confidence: 99%

Concentration‐ and Solvent‐Dependent Photochemical Instability of 6,13‐Bis(triisopropysilylethynyl)pentacene

Abu-Sen

Morrison

Horn

et al. 2014

Advanced Optical Materials

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lifetimes are also strongly environment-dependent, ranging from around 7 ns in dilute solution [ 17 ] to sub-ps in thin fi lms. [ 15 ] Direct observation of the kinetics of singlet fi ssion of TIPSpentacene in anhydrous, O 2 -free CHCl 3 solution over a range of concentrations reveals a singlet lifetime of ∼13 ns, [ 18 ] whilst a high-concentration triplet yield of 200% and triplet formation at a rate approaching the diffusion limit indicates the effi ciency of the process. Physical quenching must also be considered as a deactivation route in any condensed medium. Stability in solution is therefore controlled by the rates and quantum yields of these processes, many of which are not known. Recent reports of half-life increase by the attachment of stable radical species to pentacenes is further evidence of the importance of the initial singlet state lifetime. [ 19 ] In this communication, a systematic study of the half-life of TIPS-pentacene in a variety of air-equilibrated common solvents (including toluene, tetrahydrofuran (THF), dichloromethane, chloroform, isopropanol (IPA), decane and dodecane) by UVvisible spectroscopy at concentrations ranging from 2.5 × 10 −6 M to 2 × 10 −2 M is reported. Correlation of the variation of halflife for TIPS-pentacene photoxidation with TIPS-pentacene concentration, solubility parameters, dissolved O 2 concentrations and intermolecular distances yields important new insight into the processes involved. In particular, a non-linear concentration dependence is observed which points to a further perturbation in solution due to the onset of aggregation.UV-visible spectra for TIPS-pentacene in toluene over a range of concentrations from 270-800 nm in a 10 mm pathlength cuvette are characterized by three long-wavelength bands at 643, 592, and 549 nm ( Figure 1 a). These spectral features correspond to the known HOMO-LUMO gap with its associated vibrational structure. [ 20,21 ] The λ max values of the longest wavelength absorption do not appear to vary with concentration over the range shown but are observed to vary slightly with solvent (Supporting Information, S4.1). Upon photodegradation, these longer wavelength bands decrease with exposure whilst new features grow in below 450 nm. Mass spectra and NMR spectra confi rm that the main product is the 6,13-endoperoxide of TIPS-pentacene (Supporting Information, S1); this shows no features in the visible absorption spectra because the conjugated π-system in the product is too short (comprising 2 naphthalene rings). The new features observed below 450 nm are due to small quantities of the 5,14-endoperoxide (effectively a substituted anthracene. [ 6 ] For each sample, plots of normalized A/A 0 at 643 nm versus time were made as shown in Figure 1 b. These absorbance-time profi les were found to be reproducible to +/-5%, with all formulations showing retardation in rate beyond t 1/2 . Comparable decays were also measured in THF, dichloromethane, IPA, chloroform, dodecane and decane over the same concentration range (Supporting Information, ...

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Self-Assembly of C₃-Symmetrical Hexaaryltriindoles Driven by Solvophobic and CH−π Interactions

Cited by 41 publications

References 49 publications

New triindole-based organic semiconductors: structure-property relationships

New triindole-based organic semiconductors: structure-property relationships

Melanin‐Inspired Organic Electronics: Electroluminescence in Asymmetric Triazatruxenes

Concentration‐ and Solvent‐Dependent Photochemical Instability of 6,13‐Bis(triisopropysilylethynyl)pentacene

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Self-Assembly of C3-Symmetrical Hexaaryltriindoles Driven by Solvophobic and CH−π Interactions

Cited by 41 publications

References 49 publications

New triindole-based organic semiconductors: structure-property relationships

New triindole-based organic semiconductors: structure-property relationships

Melanin‐Inspired Organic Electronics: Electroluminescence in Asymmetric Triazatruxenes

Concentration‐ and Solvent‐Dependent Photochemical Instability of 6,13‐Bis(triisopropysilylethynyl)pentacene

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Self-Assembly of C₃-Symmetrical Hexaaryltriindoles Driven by Solvophobic and CH−π Interactions