Strain‐Promoted Reactivity of Alkyne‐Containing Cycloparaphenylenes

Schaub, Tobias A.; Margraf, Johannes T.; Zakharov, Lev N.; Reuter, Karsten; Jasti, Ramesh

doi:10.1002/anie.201808611

“…These shape‐persistent macrocycles can be prepared with varying size and atomic composition (Figure b), which has unveiled their numerous size‐dependent optoelectronic behavior and promising materials applications . In particular, owing to the tunable and bright fluorescence, biocompatibility, and metal binding capabilities,,, we have a growing interest in the development of these π‐rich macrocycles for biological applications.…”

Section: Figurementioning

confidence: 99%

Nanohoop Rotaxanes from Active Metal Template Syntheses and Their Potential in Sensing Applications

Raden

¹

,

White

²

,

Zakharov

³

et al. 2019

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The unique optoelectronic properties and smooth, rigid pores of macrocycles with radially oriented p systems render them fascinating candidates for the design of novel mechanically interlocked molecules with new properties.T wo high-yielding strategies are used to prepare nanohoop [2]rotaxanes,which owing to the p-rich macrocycle are highly emissive. Then, metal coordination, an intrinsic property afforded by the resulting mechanical bond, can lead to molecular shuttling as well as modulate the observed fluorescence in both organic and aqueous conditions.Inspired by these findings,aself-immolative [2]rotaxane was then designed that self-destructs in the presence of an analyte,e liciting as trong fluorescent turn-on response,s erving as proof-of-concept for an ew type of molecular sensing material. More broadly,this work highlights the conceptual advantages of combining compact p-rich macrocyclic frameworks with mechanical bonds formed via active-template syntheses.

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“…Alkyne‐containing [11]‐, [9]‐, and [7]CPP derivatives 26 , 27 , and 28 were prepared by Jasti and co‐workers (Figures a–c) . The Suzuki–Miyaura coupling reaction was applied to this end.…”

Section: Angle‐strained Alkyne‐containing π‐Conjugated Macrocyclesmentioning

confidence: 99%

“…[100] Alkyne-containing [11]-, [9]-, and [7]CPP derivatives 26, 27, and 28 were preparedb yJ asti and co-workers (Figures 16 ac). [101] TheS uzuki-Miyaura coupling reaction was appliedt o this end. The coupling reactione fficiently proceeded to afford the precursor 25 in 72 %y ield.…”

Section: Para-cyclophynes:ethynylene Units > Phenylene Unitsmentioning

confidence: 99%

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

Miki

¹

,

Ohe

²

2019

Chemistry A European J

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Angle‐strained alkyne‐containing π‐conjugated macrocycles are attractive compounds both in functional materials chemistry and biochemistry. Their interesting reactivity as well as photophysical and supramolecular properties have been revealed in the past three decades. This review highlights the recent advances in angle‐strained alkyne‐containing π‐conjugated macrocycles, especially their synthetic methods, the bond angles of alkynes (∠sp at C≡C−C), and their functions. The theoretical and experimental research on cyclo[n]carbons and para‐cyclophynes consisting of ethynylenes and para‐phenylenes are mainly summarized. Related macrocycles bearing other linkers, such as ortho‐phenylenes, meta‐phenylenes, heteroaromatics, biphenyls, extended aromatics, are also overviewed. Bond angles of strained alkynes in π‐conjugated macrocycles, which are generable, detectable, and isolable, are summarized at the end of this review.

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“…These shape‐persistent macrocycles can be prepared with varying size and atomic composition (Figure b), which has unveiled their numerous size‐dependent optoelectronic behavior and promising materials applications . In particular, owing to the tunable and bright fluorescence, biocompatibility, and metal binding capabilities,,, we have a growing interest in the development of these π‐rich macrocycles for biological applications.…”

Section: Figurementioning

confidence: 99%

Nanohoop Rotaxanes from Active Metal Template Syntheses and Their Potential in Sensing Applications

Raden

¹

,

White

²

,

Zakharov

³

et al. 2019

Angewandte Chemie

Self Cite

15

0

View full text Add to dashboard Cite

The unique optoelectronic properties and smooth, rigid pores of macrocycles with radially oriented p systems render them fascinating candidates for the design of novel mechanically interlocked molecules with new properties.T wo high-yielding strategies are used to prepare nanohoop [2]rotaxanes,which owing to the p-rich macrocycle are highly emissive. Then, metal coordination, an intrinsic property afforded by the resulting mechanical bond, can lead to molecular shuttling as well as modulate the observed fluorescence in both organic and aqueous conditions.Inspired by these findings,aself-immolative [2]rotaxane was then designed that self-destructs in the presence of an analyte,e liciting as trong fluorescent turn-on response,s erving as proof-of-concept for an ew type of molecular sensing material. More broadly,this work highlights the conceptual advantages of combining compact p-rich macrocyclic frameworks with mechanical bonds formed via active-template syntheses.

show abstract

Strain‐Promoted Reactivity of Alkyne‐Containing Cycloparaphenylenes

Cited by 42 publications

References 69 publications

Nanohoop Rotaxanes from Active Metal Template Syntheses and Their Potential in Sensing Applications

Nanohoop Rotaxanes from Active Metal Template Syntheses and Their Potential in Sensing Applications

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

Nanohoop Rotaxanes from Active Metal Template Syntheses and Their Potential in Sensing Applications

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