Dioxo- and aminooxopyrimidotetrathiafulvalenes: π-Electron donors for design of conducting materials containing intramolecular hydrogen bonds of nucleic acid base pair type

Neilands, O.; Tilika, V. Zh.; Sudmale, I.; Grigorjeva, I.; Edzina, A.; Fonavs, E.; Muzikante, I.

doi:10.1002/(sici)1099-0712(199703)7:2<93::aid-amo276>3.0.co;2-e

Cited by 6 publications

(3 citation statements)

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“…This consideration is consistent with the result from a very low-energy absorption band around 3000 cm -1 , which can be assigned to an intrastack CT transition in the TCNQ column with a partial ionicity (Figure d and Table ). , Room-temperature conductivity on a compressed pellet using the four-probe method is evaluated to be 0.07 S cm -1 with semiconducting behavior, which is similar to that of TU−TCNQ 7c. These two CT complexes demonstrate 10−10 orders higher conductivity than those of other CT complexes based on TTF derivatives having a variety of H-bonding functionalities (Table ) …”

supporting

confidence: 86%

Hydrogen-Bonded Charge-Transfer Complexes of TTF Containing a Uracil Moiety: Crystal Structures and Electronic Properties of the Hydrogen Cyananilate and TCNQ Complexes

et al. 2002

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[structure: see text] A novel TTF-based donor with a uracil moiety, TTF-(1-n-butyluracil-5-yl) (TnbU), was synthesized. Crystal structures of both TnbU and the charge-transfer complex of TnbU-hydrogen cyananilate possess complementary double hydrogen bonds through uracil moieties and pi-stacking dimer structures between TTF skeletons. Furthermore, the TnbU-TCNQ charge-transfer complex shows a high electrical conductivity underlying the partial charge-transfer accompanied by a hydrogen-bonding interaction, which was substantiated in terms of the measurements of the IR, electronic spectra, and conductivity.

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supporting

confidence: 86%

Hydrogen-Bonded Charge-Transfer Complexes of TTF Containing a Uracil Moiety: Crystal Structures and Electronic Properties of the Hydrogen Cyananilate and TCNQ Complexes

et al. 2002

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“…Similar to DNA, we envisioned that the complementary HB and π–π stacking interactions found in quinone-fused aza-phenazines (QAPs, Figure B) could promote a noncovalent interaction network ,− where electron transfer can occur via connected charge storage units in both longitudinal (π–π stacking) and transverse (HB) directions. − However, the C–H···X hydrogen bonds in the parent QAP scaffold are much weaker than those between heteroatomic donors and acceptors in DNA (N–H···X or O–H···X) (Figure ). Therefore, we hypothesized that QAPs functionalized with additional heteroatomic HB groups, e.g.…”

mentioning

confidence: 99%

Synergistic Effect of Hydrogen Bonding and π–π Stacking Enables Long Cycle Life in Organic Electrode Materials

2021

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Small-molecule organic compounds have emerged as attractive candidates for energy storage in lithium-ion batteries because of their sustainability and modularity. To develop generalizable design principles for organic electrode materials (OEMs), we investigated the correlation between electrochemical performance and addition of functional groups that promote synergistic hydrogen bonding and π−π stacking using a series of quinone-fused aza-phenazines (QAPs) with different hydrogen bonding donor/acceptor arrays. The QAP containing the most hydrogen bonding groups (3) exhibits the best performance with discharge capacities of 145 mAh g −1 at 2C and with 82% capacity retention over 1000 cycles. The performance of 3 is attributed to the strategically incorporated hydrogen bonding groups, which facilitate strong intermolecular interactions and a tightly packed 2D structure. The intermolecular interaction strength was evaluated using variable temperature 1D 1 H NMR and 2D 1 H− 1 H NOESY (nuclear Overhauser effect spectroscopy), offering a new strategy to help understand and predict the performance of OEMs with hydrogen bonding motifs.

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“…[20][21][22][23][24][25] Similar to DNA, we envisioned that the complementary HB and - stacking interactions found in quinone-fused aza-phenazines (QAPs, Figure 1B) could promote a non-covalent interaction network 22, [26][27][28] where electron transfer can occur via connected charge storage units in both longitudinal (- stacking) and transverse (HB) directions. [29][30][31][32][33][34][35] However, the hydrogen bonds between heteroatomic donors and acceptors in DNA (N-H … X or O-H … X) are much stronger than the weak C-H … X hydrogen bonds in the parent QAP scaffold (Figure 1). Therefore, we hypothesized that QAPs functionalized with additional heteroatomic HB groups, e.g.…”

Section: Toc Graphicmentioning

confidence: 99%

Synergistic Effect of Hydrogen Bonding and π-π Stacking Enables Long Cycle Life in Organic Electrode Materials

Tuttle¹,

Davis²,

Zhang

2020

Preprint

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Small-molecule organic compounds have emerged as attractive candidates for energy storage in lithium-ion batteries due to their sustainability and modularity. To develop generalizable design principles for organic electrode materials (OEMs), we investigated the correlation between electrochemical performance and addition of functional groups that promote synergistic hydrogen bonding and π-π stacking using a series of quinone-fused aza-phenazines (QAPs) with different hydrogen bonding donor/acceptor arrays. The QAP containing the most hydrogen bonding groups (3) exhibits the best performance with discharge capacities of 145 mAh g-1 at 2C with 82% capacity retention over 1000 cycles. The performance of 3 is attributed to the strategically incorporated -OH and -NH2 groups, which facilitate strong intermolecular interactions and a tightly packed 2D structure. The intermolecular interaction strength was evaluated using variable temperature 1D 1H NMR and 2D 1H-1H NOESY, offering a new strategy to help understand and predict the performance of OEMs with hydrogen bonding motifs.

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Dioxo- and aminooxopyrimidotetrathiafulvalenes: π-Electron donors for design of conducting materials containing intramolecular hydrogen bonds of nucleic acid base pair type

Cited by 6 publications

References 0 publications

Hydrogen-Bonded Charge-Transfer Complexes of TTF Containing a Uracil Moiety: Crystal Structures and Electronic Properties of the Hydrogen Cyananilate and TCNQ Complexes

Hydrogen-Bonded Charge-Transfer Complexes of TTF Containing a Uracil Moiety: Crystal Structures and Electronic Properties of the Hydrogen Cyananilate and TCNQ Complexes

Synergistic Effect of Hydrogen Bonding and π–π Stacking Enables Long Cycle Life in Organic Electrode Materials

Synergistic Effect of Hydrogen Bonding and π-π Stacking Enables Long Cycle Life in Organic Electrode Materials

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