A BN‐Doped Cycloparaphenylene Debuts

Chen, Min; Unikela, Kiran Sagar; Ramalakshmi, Rongala; Li, Bo; Darrigan, Clovis; Chrostowska, Anna; Liu, Shih‐Yuan

doi:10.1002/ange.202010556

Cited by 20 publications

(5 citation statements)

References 63 publications

(86 reference statements)

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“…To tune their molecular properties, CPPs have been chemically modified. In this context, the substitution of hydrogen by halides [19–26] as well as carbon by nitrogen [27–32] have been achieved. Additionally, introduction of electron‐donating or withdrawing groups [33] and larger π‐frameworks [34] into the ring molecule have been reported.…”

Section: Introductionmentioning

confidence: 99%

Two Rings Around One Ball: Stability and Charge Localization of [1 : 1] and [2 : 1] Complex Ions of [10]CPP and C_60/70^[*^]

Freiberger

Minameyer

Solymosi

et al. 2023

Chemistry A European J

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We investigate the gas-phase chemistry of noncovalent complexes of [10]cycloparaphenylene ([10]CPP) with C 60 and C 70 by means of atmospheric pressure photoionization and electrospray ionization mass spectrometry. The literature-known [1 : 1] complexes, namely [10]CPP�C 60 and [10]CPP�C 70 , are observed as radical cations and anions. Their stability and charge distribution are studied using energyresolved collision-induced dissociation (ER-CID). These measurements reveal that complexes with a C 70 core exhibit a greater stability and, on the other hand, that the radical cations are more stable than the respective radical anions. Regarding the charge distribution, in anionic complexes charges are exclusively located on C 60 or C 70 , while the charges reside on [10]CPP in the case of cationic complexes.[2 : 1] complexes of the ([10]CPP 2 �C 60/70 ) + */À * type are observed for the first time as isolated solitary gas-phase species.Here, C 60 -based [2 : 1] complexes are less stable than the respective C 70 analogues. By virtue of the high stability of cationic [1 : 1] complexes, [2 : 1] complexes show a strongly reduced stability of the radical cations. DFT analyses of the minimum geometries as well as molecular dynamics calculations support the experimental data. Furthermore, our novel gas-phase [2 : 1] complexes are also found in 1,2-dichlorobenzene. Insights into the thermodynamic parameters of the binding process as well as the species distribution are derived from isothermal titration calorimetry (ITC) measurements.

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Section: Introductionmentioning

confidence: 99%

Two Rings Around One Ball: Stability and Charge Localization of [1 : 1] and [2 : 1] Complex Ions of [10]CPP and C_60/70^[*^]

Freiberger

Minameyer

Solymosi

et al. 2023

Chemistry A European J

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“…In 2021, the Liu group employed 1,2‐azaborine BN heterocycle derivative to replace a phenyl unit of [10]CPP scaffold, and successfully built the BN‐doped cycloparaphenylene 17 (Figure 13). [24] Although the optoelectronic properties of macrocycle 17 were similar to its all‐carbon [10]CPP, the reactivity of 17 was dramatically enhanced. This B−N heterocycle undergoes selective hydrogenation under mild conditions (RT, 1.0 atm H 2 ).…”

Section: B/n‐doped Macrocycles In Light‐emitting Materialsmentioning

confidence: 99%

Section: B/n‐doped Macrocycles In Light‐emitting Materialsmentioning

confidence: 99%

Design and Synthesis of New Type of Macrocyclic Architectures Used for Optoelectronic Materials and Supramolecular Chemistry

Jia

Chen

2023

Chemistry A European J

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Supramolecular chemistry has received much attention for decades. Macrocyclic architectures as representative receptors play a vital role in supramolecular chemistry and are applied in many fields such as supramolecular assembly and host‐guest recognition. However, the classical macrocycles generally lack functional groups in the scaffolds, which limit their further applications, especially in optoelectronic materials. Therefore, developing new design principle is not only essential to better understand macrocyclic chemistry and the supramolecular behaviors, but also further expand their applications in many research fields. In recent years, the doping compounds with main‐group heteroatoms (B, N, S, O, P) into the carbon‐based π‐conjugated macrocycles offered a new strategy to build macrocyclic architectures with unique optoelectronic properties. In particular, the energy gaps and redox behavior can be effectively tuned by incorporating heteroatoms into the macrocyclic scaffolds. In this Minireview, we briefly summarize the design and synthesis of new macrocycles, and further discuss the related applications in optoelectronic materials and supramolecular chemistry.

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“…The introduction of heteroatoms into the conjugated systems is an important means to the design and synthesis of novel structures [5] . To date, a number of heterocyclic CPPs have been synthesized including pyridine, thiophene, selenyl benzene, furan, perylene diimide, and porphyrin 1,2‐nitrogen heterocycles; [6] however, only one boron‐atom‐embedded CPP has been reported [7] …”

Section: Figurementioning

confidence: 99%

Boron‐Cluster Embedded Necklace‐Shaped Nanohoops

Zhu

Zhou

et al. 2022

Angew Chem Int Ed

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The combination of carbon‐based nanohoops with other functional organic molecular structures should lead to the design of new molecular configurations with interesting properties. Here, necklace‐like nanohoops embedded with carborane were synthesized for the first time. The unique deboronization of o‐carborane has led to the facile preparation of ionic nanohoop compounds. Nanohoops functionalized by nido‐o‐carborane show excellent fluorescence emission, with a solution quantum yield of up to 90.0 % in THF and a solid‐state quantum efficiency of 87.3 %, which opens an avenue for the applications of the nanohoops in OLEDs and bioimaging.

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A BN‐Doped Cycloparaphenylene Debuts

Abstract: and by Boston College start-up funds. K.S.U. thanks Mario Sokolic for assistance with the preparation of synthetic building blocks.

Cited by 20 publications

References 63 publications

Two Rings Around One Ball: Stability and Charge Localization of [1 : 1] and [2 : 1] Complex Ions of [10]CPP and C_60/70^[*^]

Two Rings Around One Ball: Stability and Charge Localization of [1 : 1] and [2 : 1] Complex Ions of [10]CPP and C_60/70^[*^]

Design and Synthesis of New Type of Macrocyclic Architectures Used for Optoelectronic Materials and Supramolecular Chemistry

Boron‐Cluster Embedded Necklace‐Shaped Nanohoops

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A BN‐Doped Cycloparaphenylene Debuts

Abstract: and by Boston College start-up funds. K.S.U. thanks Mario Sokolic for assistance with the preparation of synthetic building blocks.

Cited by 20 publications

References 63 publications

Two Rings Around One Ball: Stability and Charge Localization of [1 : 1] and [2 : 1] Complex Ions of [10]CPP and C60/70[*]

Two Rings Around One Ball: Stability and Charge Localization of [1 : 1] and [2 : 1] Complex Ions of [10]CPP and C60/70[*]

Design and Synthesis of New Type of Macrocyclic Architectures Used for Optoelectronic Materials and Supramolecular Chemistry

Boron‐Cluster Embedded Necklace‐Shaped Nanohoops

Contact Info

Product

Resources

About

Two Rings Around One Ball: Stability and Charge Localization of [1 : 1] and [2 : 1] Complex Ions of [10]CPP and C_60/70^[*^]

Two Rings Around One Ball: Stability and Charge Localization of [1 : 1] and [2 : 1] Complex Ions of [10]CPP and C_60/70^[*^]