TY - JOUR
T1 - Macrocyclic Oligofurans
T2 - A Computational Study
AU - Dishi, Or
AU - Gidron, Ori
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/3/16
Y1 - 2018/3/16
N2 - Macrocyclic oligothiophenes (nCT) have been extensively explored for their unique optical and electronic properties, while their oxygen-containing analogues, macrocyclic oligofurans (nCF), are not known. In this work, macrocyclic oligofurans bearing 5-16 units (5CF-16CF) are studied theoretically at the B3LYP/6-311G(d) level. We find that small macrocycles (6CF-8CF) exhibit planar or nearly planar geometries, low strain energies, low HOMO-LUMO gaps, and strong π-conjugation as also reflected in their Raman spectra. These findings are in sharp contrast to macrocyclic oligothiophenes of the same size, which are distorted from planarity. Additionally, small macrocyclic furans display significantly lower reorganization energies and ionization potentials compared with their thiophene analogues. Overall, the observed properties highlight the potential of macrocyclic oligofurans to function as p-type organic electronic materials.
AB - Macrocyclic oligothiophenes (nCT) have been extensively explored for their unique optical and electronic properties, while their oxygen-containing analogues, macrocyclic oligofurans (nCF), are not known. In this work, macrocyclic oligofurans bearing 5-16 units (5CF-16CF) are studied theoretically at the B3LYP/6-311G(d) level. We find that small macrocycles (6CF-8CF) exhibit planar or nearly planar geometries, low strain energies, low HOMO-LUMO gaps, and strong π-conjugation as also reflected in their Raman spectra. These findings are in sharp contrast to macrocyclic oligothiophenes of the same size, which are distorted from planarity. Additionally, small macrocyclic furans display significantly lower reorganization energies and ionization potentials compared with their thiophene analogues. Overall, the observed properties highlight the potential of macrocyclic oligofurans to function as p-type organic electronic materials.
UR - http://www.scopus.com/inward/record.url?scp=85044094008&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b03030
DO - 10.1021/acs.joc.7b03030
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C2 - 29457897
AN - SCOPUS:85044094008
SN - 0022-3263
VL - 83
SP - 3119
EP - 3125
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 6
ER -