Columnar self-assembly of star-shaped luminescent oxadiazole and thiadiazole derivatives

Pathak, Suraj Kumar; Gupta, Ravindra; Nath, Subrata; Rao, D. S. Shankar; Prasad, S. Krishna; Achalkumar, Ammathnadu S.

doi:10.1039/c5tc00009b

Cited by 80 publications

(33 citation statements)

References 154 publications

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“…4). 31 1,3,4-Oxadiazole-based SSMs 123a,b were synthesized as outlined in Scheme 31 via rstly reaction of 4-((3,4-bis(alkoxy) phenyl)ethynyl)benzonitrile 121a or 121b with sodium azide to afford tetrazole derivatives 122a and 122b, respectively, in excellent yields (85-90%). Synthesis of 123a and 123b was then achieved via treating 122a and 122b, respectively, with trimesic acid chloride 109 by a typical Huisgen reaction mechanism.…”

Section: Ssms With Alicyclic Coresmentioning

confidence: 99%

“…In 1948, Schaefgen and Flory reported formation of mesophases of interesting mesomorphic and photophysical properties. [18][19][20][21][22][23][24][25][26][27][28][29][30][31] The applications of starshaped molecules as building units for dendrimers 32,33 as well as in supramolecular host-guest chemistry have been also reported. 34,35 Moreover, the interesting biological activities of some diverse multivalent scaffolds adamantane have been recently investigated.…”

Section: Introductionmentioning

confidence: 99%

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An overview on synthetic strategies for the construction of star-shaped molecules

et al. 2019

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Section: Ssms With Alicyclic Coresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

An overview on synthetic strategies for the construction of star-shaped molecules

et al. 2019

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“…In recent years, a rapid development has occurred in the field of p-conjugated organic semiconductors owing to promising aspects of their application in organic electronic and optoelectronic devices [1][2][3][4] such as: Organic Field Effect Transistors (OFET), 3,5 Organic Light Emitting Diodes (OLED), [6][7][8][9] Organic Photovoltaic cells (OPV) [10][11][12] and Electrochromic Devices (ECD). [13][14][15] The peculiar electron transport, 16,17 optical, 18 photo- 19,20 or electro-luminescent [21][22][23] and redox properties of these materials originate from their distinctive electronic structure.…”

Section: Introductionmentioning

confidence: 99%

Effect of donor to acceptor ratio on electrochemical and spectroscopic properties of oligoalkylthiophene 1,3,4-oxadiazole derivatives

Kurowska

Zassowski

Kostyuchenko

et al. 2017

Phys. Chem. Chem. Phys.

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A structure-property study across a series of donor-acceptor-donor structures composed of mono- and bi-(1,3,4-oxadiazole) units symmetrically substituted with alkyl functionalized bi-, ter- and quaterthiophene segments is presented. Synthetically tailoring the ratio of electron-withdrawing 1,3,4-oxadiazole to electron-releasing thiophene units and their alkyl grafting pattern permitted us to scrutinize the impact of these structural factors on the redox, absorptive and emissive properties of these push-pull molecules. Contrasting trends of redox potentials were observed, with the oxidation potential closely following the donor-to-acceptor ratio, whereas the reduction potential being tuned independently by either the number of acceptor units or the conjugation length of the donor-acceptor system. Increasing the thiophene unit contribution delivered a shift from blue to green luminescence, while the structural rigidity afforded by intramolecular non-covalent interactions between 1,3,4-oxadiazole and the thiophene moieties has been identified as the prime factor determining the emission efficiency of these molecules. All six structures investigated electro-polymerize easily, yielding electroactive and electrochromic polymers. The polymer doping process is largely influenced by the length of the oligothiophene repeating unit and the alkyl chain grafting density. Polymers with relatively short oligothiophene segments are able to support polarons and polaron-pairs, whereas those with segments longer than six thiophene units could also stabilize diamagnetic charge carries - bipolarons. Increasing the alkyl chain grafting density improved the reversibility and broadened the working potential window of the p-doping process. Stable radical anions have also been investigated, bringing detailed information about the conjugation pattern of these electron-surplus species. This study delivers interesting clues towards the conscious structural design of bespoke frontier energy level oligothiophene functional materials and their polymers by incorporating a structurally matching 1,3,4-oxadiazole unit.

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“…32,33 The observed larger red shift in the absorption and emission of thiadiazole compounds is ascribed to the higher polarizability and also attributed to the basic nature of sulphur atom in the thiadiazole moiety compared to the oxadiazole compounds. 34 In the entire series of compounds, 5a-5d and 6a-6d, with increasing length of alkoxy chain, there is no change in wavelength of absorption and emission bands as the increase in the alkoxy terminal chain does not influence on photophysical properties.…”

Section: Photophysical Propertiesmentioning

confidence: 95%

Bent Shaped 1,3,4-Oxadiazole/Thiadiazole heterocyclic rings containing liquid crystals

Selvarasu

Kannan

2015

J Chem Sci

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Two series of bent shaped 1,3,4-oxadiazole/thiadiazole heterocyclic ring containing liquid crystalline (LC) compounds were synthesized and characterized by FT-IR, 1 H, 13 C-NMR and ESI-Mass spectroscopic techniques. Liquid crystal properties were investigated by polarized optical microscopy and differential scanning calorimetry. All the compounds exhibited mesophases such as nematic, smectic A and smectic C phases. The liquid crystalline effects were ascertained by changing the central atom in the heterocyclic ring and by increasing the length of the terminal alkyloxy chains which bring considerable improvements on the mesomorphic properties. The absorption and emission spectral studies of all the compounds were investigated and confirmed.

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Columnar self-assembly of star-shaped luminescent oxadiazole and thiadiazole derivatives

Abstract: Blue light emitting star-shaped oxadiazole and thiadiazoles stabilizing fluid columnar phase.

Cited by 80 publications

References 154 publications

An overview on synthetic strategies for the construction of star-shaped molecules

An overview on synthetic strategies for the construction of star-shaped molecules

Effect of donor to acceptor ratio on electrochemical and spectroscopic properties of oligoalkylthiophene 1,3,4-oxadiazole derivatives

Bent Shaped 1,3,4-Oxadiazole/Thiadiazole heterocyclic rings containing liquid crystals

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