Abstract
The synthesis of C4- and C2-symmetrical [8]cycloparaphenylene (CPP)-octacarboxylates has been achieved via macrocyclization by the rhodium-catalyzed intermolecular stepwise cross-cyclotrimerization and subsequent reductive aromatization. The C4-symmetrical octa-tert-butyl [8]CPP-octacarboxylate forms a dimer in which eight ester moieties face each other. The dimers are aligned so as to make a one-dimensional column with a channel structure inside. Both absorption and fluorescence maxima of [8]CPP-octacarboxylates in CHCl3 were significantly blue-shifted compared to those of [8]CPP due to the presence of eight electron-withdrawing ester moieties.
| Original language | English |
|---|---|
| Pages (from-to) | 2993-2996 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 19 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 2017 Jun 2 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Synthesis of [8]Cycloparaphenylene-octacarboxylates via Rh-Catalyzed Stepwise Cross-Alkyne Cyclotrimerization. / Hayase, Norihiko; Miyauchi, Yuta; Aida, Yukimasa; Sugiyama, Haruki; Uekusa, Hidehiro; Shibata, Yu; Tanaka, Ken.
In: Organic Letters, Vol. 19, No. 11, 02.06.2017, p. 2993-2996.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Synthesis of [8]Cycloparaphenylene-octacarboxylates via Rh-Catalyzed Stepwise Cross-Alkyne Cyclotrimerization
AU - Hayase, Norihiko
AU - Miyauchi, Yuta
AU - Aida, Yukimasa
AU - Sugiyama, Haruki
AU - Uekusa, Hidehiro
AU - Shibata, Yu
AU - Tanaka, Ken
PY - 2017/6/2
Y1 - 2017/6/2
N2 - The synthesis of C4- and C2-symmetrical [8]cycloparaphenylene (CPP)-octacarboxylates has been achieved via macrocyclization by the rhodium-catalyzed intermolecular stepwise cross-cyclotrimerization and subsequent reductive aromatization. The C4-symmetrical octa-tert-butyl [8]CPP-octacarboxylate forms a dimer in which eight ester moieties face each other. The dimers are aligned so as to make a one-dimensional column with a channel structure inside. Both absorption and fluorescence maxima of [8]CPP-octacarboxylates in CHCl3 were significantly blue-shifted compared to those of [8]CPP due to the presence of eight electron-withdrawing ester moieties.
AB - The synthesis of C4- and C2-symmetrical [8]cycloparaphenylene (CPP)-octacarboxylates has been achieved via macrocyclization by the rhodium-catalyzed intermolecular stepwise cross-cyclotrimerization and subsequent reductive aromatization. The C4-symmetrical octa-tert-butyl [8]CPP-octacarboxylate forms a dimer in which eight ester moieties face each other. The dimers are aligned so as to make a one-dimensional column with a channel structure inside. Both absorption and fluorescence maxima of [8]CPP-octacarboxylates in CHCl3 were significantly blue-shifted compared to those of [8]CPP due to the presence of eight electron-withdrawing ester moieties.
UR - http://www.scopus.com/inward/record.url?scp=85020020217&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85020020217&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.7b01231
DO - 10.1021/acs.orglett.7b01231
M3 - Article
AN - SCOPUS:85020020217
VL - 19
SP - 2993
EP - 2996
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 11
ER -