2018
DOI: 10.1002/chem.201704825
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Supramolecular Chirality Issues in Unorthodox Naphthalene Diimide Gelators

Abstract: Herein, the self-assembly of a few 1,3-dihydroxyl functionalized naphthalene diimide (NDI) derivatives has been reported with particular emphasis on the impact of chirality on gelation and the effect of self-assembly on charge-carrier mobility. A nonconventional gelator (R)-NDI, devoid of any long alkyl chains, exhibited spontaneous gelation in tetra-chloroethylene (TCE). Based on X-ray crystallography and powder X-ray diffraction studies, it was established that a ladder-like hydrogen-bonded chain formation b… Show more

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Cited by 20 publications
(14 citation statements)
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“…This is due to the high sensitivity of H‐bonds to external stimuli and their environment. Chirality can impact the self‐assembly properties as well, and in the case of semiconductors their optoelectronic properties . The chirality is amplified when the molecular chirality is transferred to the supramolecular structures, making new properties emerge.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…This is due to the high sensitivity of H‐bonds to external stimuli and their environment. Chirality can impact the self‐assembly properties as well, and in the case of semiconductors their optoelectronic properties . The chirality is amplified when the molecular chirality is transferred to the supramolecular structures, making new properties emerge.…”
Section: Introductionmentioning
confidence: 99%
“…The chirality is amplified when the molecular chirality is transferred to the supramolecular structures, making new properties emerge. Supramolecular chirality has been explored in organic semiconductors using π–π stacking and H‐bonding mainly . In this work, we explore hydrogen‐bonded diketopyrrolopyrrole (DPP) derivatives containing chiral and achiral centers.…”
Section: Introductionmentioning
confidence: 99%
“…Interestingly, the gel formed from a mixture of L,L,L and D,D,D has similar values to that formed with L,L,L alone, explaining why the two samples have similar T gel and T 100% values. This provides further evidence suggesting that the complex formed between L,L,L and C8R is capable of directing the aggregation of the mixed L,L,L/D,D,D system in a manner reminiscent of the ‘majority rules’ mechanism [67,68,69,70,71,72,73,74].…”
Section: Resultsmentioning
confidence: 77%
“…This can be assigned to a thermodynamic preference for heterochiral interactions—either at the molecular- or nanoscale. Chiral directing effects have also been reported in which a small amount of chiral additive can impose its preference onto an achiral system (a “sergeants and soldiers” effect), or a small excess of one enantiomer can impose its preference onto the other (a “majority rules” effect) [67,68,69,70,71,72,73,74].…”
Section: Introductionmentioning
confidence: 99%
“…Unexpectedly, mixing both achiral 1 and chiral (S)-2 results in a completely different dichroic pattern to that registered for the pristine sergeant, a phenomenon that has been rarely reported in the literature. 21 The CD spectra of the mixture display a negative band at λ ¼ 258 nm and two positive bands at λ ¼ 335 and 365 nm with an isodichroic point at λ ¼ 278 nm (Figures 3 and S5a).…”
Section: Resultsmentioning
confidence: 99%