The lithium‐orientation effect on the hyperpolarizability in the short zigzag‐edged monolithiated aza‐Möbius graphene ribbon [2,7] isomers

Wang, Yinfeng; Wang, Yi; Li, Zhi‐Ru; Li, Zhuo; Xu, Hong‐Liang; Sun, Chia‐Chung

doi:10.1002/qua.22525

Cited by 15 publications

(24 citation statements)

References 41 publications

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“…for a previously reported nitrogen‐substituted MC,6a 352–1019 a.u. for an Li‐monosubstituted aza‐Möbius graphene ribbon,19 and 3773 a.u. for a Möbius basket molecule 5c.…”

Section: Resultsmentioning

confidence: 99%

Spiral Intramolecular Charge Transfer and Large First Hyperpolarizability in Möbius Cyclacenes: New Insight into the Localized π Electrons

Zhong

et al. 2012

ChemPhysChem

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Much effort has been devoted to investigating the unusual properties of the π electrons in Möbius cyclacenes, which are localized in a special region. However, the localized π electrons are a disadvantage for applications in optoelectronics, because intramolecular charge transfer is limited. This raises the question of how the intramolecular charge transfer of a Möbius cyclacene with clearly localized π electrons can be enhanced. To this end, [8]Möbius cyclacene ([8]MC) is used as a conjugated bridge in a donor-π-conjugated bridge-acceptor (D-π-A) system, and NH(2)-6-[8]MC-10-NO(2) exhibits a fascinating spiral charge-transfer transition character that results in a significant difference in dipole moments Δμ between the ground state and the crucial excited state. The Δμ value of 6.832 D for NH(2)-6-[8]MC-10-NO(2) is clearly larger than that of 0.209 D for [8]MC. Correspondingly, the first hyperpolarizability of NH(2)-6-[8]MC-10-NO(2) of 12,467 a.u. is dramatically larger than that of 261 a.u. for [8]MC. Thus, constructing a D-π-A framework is an effective strategy to induce greater spiral intramolecular charge transfer in MC although the π electrons are localized in a special region. This new insight into the properties of π electrons in Möbius cyclacenes may provide valuable information for their applications in optoelectronics.

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“…for a previously reported nitrogen‐substituted MC,6a 352–1019 a.u. for an Li‐monosubstituted aza‐Möbius graphene ribbon,19 and 3773 a.u. for a Möbius basket molecule 5c.…”

Section: Resultsmentioning

confidence: 99%

Spiral Intramolecular Charge Transfer and Large First Hyperpolarizability in Möbius Cyclacenes: New Insight into the Localized π Electrons

Zhong

et al. 2012

ChemPhysChem

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“…For this purpose, it has been well-established in the literature that the computational theoryaided design can be a useful tool to optimize the molecular electro-optic performance. [28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44] Recently, several works [45][46][47][48][49][50][51][52][53][54][55] have evaluated the NLOP of Hückel and Möbius topologies. For instance, the present authors studied the electronic and vibrational contributions to static and dynamic NLOP of the Hückel-Möbius switch of the bianthraquinodimethane modified [16] annulene 56,57 and A,D-di-p-benzi [28]hexaphyrin(1.1.1.1.1.1).…”

Section: ) Introductionmentioning

confidence: 99%

Design of Hückel–Möbius Topological Switches with High Nonlinear Optical Properties

et al. 2017

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The macrocyclic ring of expanded porphyrins presents a conformational versatility that leads to original structural motifs and generates unique Hückel-to-Möbius topological switches. These systems can act as optoelectronic materials and their range of applicability depends on the high values of the nonlinear optical properties (NLOP) and the large differences between the Hückel and Möbius structures. With the aim to design new topological switches with the optimum NLOP, we have performed a DFT computational study on the effect of three different geometric and electronic factors of the meso-substituents: i) their electron-withdrawing and -releasing character; ii) their distribution along

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“…Xu et al 13 studied the electronic dipole moment and first hyperpolarizability of aza- [7]cyclacenes with/without a knot and four knots isomers of strip aza- [15]cyclacenes. In addition, Wang et al 14 reported the electronic first hyperpolarizability of a Möbius basket molecule based on six fused five-membered pyrrole rings.…”

Section: Introductionmentioning

confidence: 99%

“…In addition, Wang et al 14 reported the electronic first hyperpolarizability of a Möbius basket molecule based on six fused five-membered pyrrole rings. Wang et al 15 described the lithium-effect on the NLOP in the short zigzag-edged monolithiated aza-Möbius grapheme ribbon [2,7] isomers. Finally, the present authors 16 studied the electronic and vibrational contributions to static and dynamic NLOP of the C S Hückel and C 2 Möbius conformers of the bianthraquinodimethane modified [16] annulene synthesized by Herges and coworkers.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the nonlinear optical properties for an expanded porphyrin Hückel-Möbius aromaticity switch

Torrent‐Sucarrat

Anglada²,

Luis³

2012

The Journal of Chemical Physics

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The conformational flexibility of the expanded porphyrins allows them to achieve different topologies with distinct aromaticities and nonlinear optical properties (NLOP). For instance, it is possible to switch between Möbius and Hückel topologies applying only small changes in the external conditions or in the structure of the ring. In this work, we evaluate the electronic and vibrational contributions to static and dynamic NLOP of the Hückel and Möbius conformers of A,D-di-pbenzi[28]hexaphyrin(1.1.1.1.1.1) synthesized by Latos-Grażyński and co-workers [Angew. Chem., Int. Ed. 46, 7869 (2007)]. Calculations are performed at the HF, M052X, and CAM-B3LYP levels using the 6-31G, 6-311G(d), and 6-31+G(d) basis sets. Our results conclude that M052X/6-31G and CAM-B3LYP/6-31G methods provide a correct qualitative description of the electronic and vibrational contributions for the NLOP of expanded porphyrins. The studied systems show high NLOP with large differences between the Möbius and Hückel conformations (around 1 × 10 6 a.u. forγ ). The obtained results indicate that the expanded porphyrins are promising systems to manufacture Hückel-to-Möbius topological switches.

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The lithium‐orientation effect on the hyperpolarizability in the short zigzag‐edged monolithiated aza‐Möbius graphene ribbon [2,7] isomers

Cited by 15 publications

References 41 publications

Spiral Intramolecular Charge Transfer and Large First Hyperpolarizability in Möbius Cyclacenes: New Insight into the Localized π Electrons

Spiral Intramolecular Charge Transfer and Large First Hyperpolarizability in Möbius Cyclacenes: New Insight into the Localized π Electrons

Design of Hückel–Möbius Topological Switches with High Nonlinear Optical Properties

Evaluation of the nonlinear optical properties for an expanded porphyrin Hückel-Möbius aromaticity switch

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