Abstract
A series of indolocarbazole-pyridine (IP) hybrid foldamers containing chiral residues at multiple different positions were prepared to reveal the matched and mismatched phenomena of local stereocenters on the induction of helical bias. These foldamers adopted stable helical conformations, thus affording well-resolved separate sets of 1H NMR signals for right- (P) and left-handed (M) helices in water saturated organic solvents such as toluene and dichloromethane. The ratios of P- and M-helices were determined by integrating the 1H NMR signals, in combination with the molar circular dichroism (Δ ϵ) and optical rotation ([α]D) values. The degree of helical bias was larger in the IP foldamer bearing chiral residues at the termini relative to those at the pyridine side chains, but the preferred helix orientation was opposite to each other. Foldamers 5(SS)t(SSS)py and 6(RR)t(SSS)py with chiral residues at five different positions demonstrated the matched and mismatched phenomena of local stereocenters in 6(RR)t(SSS)py and 5(SS)t(SSS)py, respectively.
| Original language | English |
|---|---|
| Pages (from-to) | 5123-5131 |
| Number of pages | 9 |
| Journal | Journal of Organic Chemistry |
| Volume | 83 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2018 May 4 |
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All Science Journal Classification (ASJC) codes
- Organic Chemistry
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Matched and Mismatched Phenomena in the Helix Orientation Bias Induced by Chiral Appendages at Multiple Positions of Indolocarbazole-Pyridine Hybrid Foldamers. / Jang, Han Bit; Choi, Ye Rin; Jeong, Kyu Sung.
In: Journal of Organic Chemistry, Vol. 83, No. 9, 04.05.2018, p. 5123-5131.Research output: Contribution to journal › Article
TY - JOUR
T1 - Matched and Mismatched Phenomena in the Helix Orientation Bias Induced by Chiral Appendages at Multiple Positions of Indolocarbazole-Pyridine Hybrid Foldamers
AU - Jang, Han Bit
AU - Choi, Ye Rin
AU - Jeong, Kyu Sung
PY - 2018/5/4
Y1 - 2018/5/4
N2 - A series of indolocarbazole-pyridine (IP) hybrid foldamers containing chiral residues at multiple different positions were prepared to reveal the matched and mismatched phenomena of local stereocenters on the induction of helical bias. These foldamers adopted stable helical conformations, thus affording well-resolved separate sets of 1H NMR signals for right- (P) and left-handed (M) helices in water saturated organic solvents such as toluene and dichloromethane. The ratios of P- and M-helices were determined by integrating the 1H NMR signals, in combination with the molar circular dichroism (Δ ϵ) and optical rotation ([α]D) values. The degree of helical bias was larger in the IP foldamer bearing chiral residues at the termini relative to those at the pyridine side chains, but the preferred helix orientation was opposite to each other. Foldamers 5(SS)t(SSS)py and 6(RR)t(SSS)py with chiral residues at five different positions demonstrated the matched and mismatched phenomena of local stereocenters in 6(RR)t(SSS)py and 5(SS)t(SSS)py, respectively.
AB - A series of indolocarbazole-pyridine (IP) hybrid foldamers containing chiral residues at multiple different positions were prepared to reveal the matched and mismatched phenomena of local stereocenters on the induction of helical bias. These foldamers adopted stable helical conformations, thus affording well-resolved separate sets of 1H NMR signals for right- (P) and left-handed (M) helices in water saturated organic solvents such as toluene and dichloromethane. The ratios of P- and M-helices were determined by integrating the 1H NMR signals, in combination with the molar circular dichroism (Δ ϵ) and optical rotation ([α]D) values. The degree of helical bias was larger in the IP foldamer bearing chiral residues at the termini relative to those at the pyridine side chains, but the preferred helix orientation was opposite to each other. Foldamers 5(SS)t(SSS)py and 6(RR)t(SSS)py with chiral residues at five different positions demonstrated the matched and mismatched phenomena of local stereocenters in 6(RR)t(SSS)py and 5(SS)t(SSS)py, respectively.
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U2 - 10.1021/acs.joc.8b00482
DO - 10.1021/acs.joc.8b00482
M3 - Article
AN - SCOPUS:85046542031
VL - 83
SP - 5123
EP - 5131
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 9
ER -