Synthesis of Cyclic Porphyrin Trimers through Alkyne Metathesis Cyclooligomerization and Their Host-Guest Binding Study

Hai Long; Chao Yu; Yinghua Jin; Wei Zhang

doi:10.1021/acs.orglett.6b01293

Synthesis of Cyclic Porphyrin Trimers through Alkyne Metathesis Cyclooligomerization and Their Host-Guest Binding Study

Hai Long, Chao Yu, Yinghua Jin, Wei Zhang

Computational Science

University of Colorado Boulder

Research output: Contribution to journal › Article › peer-review

42 Scopus Citations

Abstract

Cyclic porphyrin trimers were synthesized through one-step cyclooligomerization via alkyne metathesis from diyne monomers. These macrocycles show interesting host-guest binding interactions with fullerenes, selectively binding C₇₀ (6 × 10³ M^-1) over C₆₀ and C₈₄ (no binding observed). The fullerene-encapsulated host-guest complex can undergo guest or host exchange in the presence of another guest (2,4,6-tri(4-pyridyl)-1,3,5-triazine) or host (cage COP5) molecule with higher binding affinity.

Original language	American English
Pages (from-to)	2946-2949
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.6b01293 https://doi.org/10.1021/acs.orglett.6b01293
State	Published - 17 Jun 2016

Bibliographical note

Publisher Copyright:
© 2016 American Chemical Society.

NREL Publication Number

NREL/JA-2C00-66644

Keywords

alkyne metathesis
cyclic porphyrin trimers
cyclooligomerization
synthesis

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title = "Synthesis of Cyclic Porphyrin Trimers through Alkyne Metathesis Cyclooligomerization and Their Host-Guest Binding Study",

abstract = "Cyclic porphyrin trimers were synthesized through one-step cyclooligomerization via alkyne metathesis from diyne monomers. These macrocycles show interesting host-guest binding interactions with fullerenes, selectively binding C70 (6 × 103 M-1) over C60 and C84 (no binding observed). The fullerene-encapsulated host-guest complex can undergo guest or host exchange in the presence of another guest (2,4,6-tri(4-pyridyl)-1,3,5-triazine) or host (cage COP5) molecule with higher binding affinity.",

keywords = "alkyne metathesis, cyclic porphyrin trimers, cyclooligomerization, synthesis",

author = "Hai Long and Chao Yu and Yinghua Jin and Wei Zhang",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

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day = "17",

doi = "10.1021/acs.orglett.6b01293",

language = "American English",

volume = "18",

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T1 - Synthesis of Cyclic Porphyrin Trimers through Alkyne Metathesis Cyclooligomerization and Their Host-Guest Binding Study

AU - Long, Hai

AU - Yu, Chao

AU - Jin, Yinghua

AU - Zhang, Wei

PY - 2016/6/17

Y1 - 2016/6/17

N2 - Cyclic porphyrin trimers were synthesized through one-step cyclooligomerization via alkyne metathesis from diyne monomers. These macrocycles show interesting host-guest binding interactions with fullerenes, selectively binding C70 (6 × 103 M-1) over C60 and C84 (no binding observed). The fullerene-encapsulated host-guest complex can undergo guest or host exchange in the presence of another guest (2,4,6-tri(4-pyridyl)-1,3,5-triazine) or host (cage COP5) molecule with higher binding affinity.

AB - Cyclic porphyrin trimers were synthesized through one-step cyclooligomerization via alkyne metathesis from diyne monomers. These macrocycles show interesting host-guest binding interactions with fullerenes, selectively binding C70 (6 × 103 M-1) over C60 and C84 (no binding observed). The fullerene-encapsulated host-guest complex can undergo guest or host exchange in the presence of another guest (2,4,6-tri(4-pyridyl)-1,3,5-triazine) or host (cage COP5) molecule with higher binding affinity.

KW - alkyne metathesis

KW - cyclic porphyrin trimers

KW - cyclooligomerization

KW - synthesis

UR - https://www.scopus.com/pages/publications/84975316954

U2 - 10.1021/acs.orglett.6b01293

DO - 10.1021/acs.orglett.6b01293

M3 - Article

AN - SCOPUS:84975316954

SN - 1523-7060

VL - 18

SP - 2946

EP - 2949

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Synthesis of Cyclic Porphyrin Trimers through Alkyne Metathesis Cyclooligomerization and Their Host-Guest Binding Study

Abstract

Bibliographical note

NREL Publication Number

Keywords

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