Related Experiment Video
Updated: May 4, 2026

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
Published on: October 10, 2016
Isomeric thiophene-fused benzocarborane molecules--different lithium doping effect on the nonlinear optical property
Yong Li1, Hong-Liang Xu, Heng-Qing Wu
1Institute of Functional Material Chemistry, Faculty of Chemistry, Northeast Normal University, Changchun 130024, Jilin, People's Republic of China. sunsl430@nenu.edu.cn zmsu@nenu.edu.cn.
Abstract:
Recently, two isomeric thiophene-fused benzocarborane derivatives Tb1 and Tb2 with different locations of sulfur atoms, labeled as 1, 4 and 6, 9 of the thiophene were synthesized by Morisaki (Chem.-Eur. J., 2012, 18, 11251-11257) and Barrere (Macromolecules, 2009, 42, 2981-2987), respectively. In the present work, natural bond orbital (NBO) analysis shows that after doping one lithium atom into the isomeric structures Tb1 and Tb2, the electrons transfer to different regions in Tb1 and Tb2. For Tb1-Li, the transferred electrons mainly locate at S1, C2, C3, and S4, but for Tb2-Li, the transferred electrons mainly locate at C2, C3, C7, and C8. Significantly, the charge distribution is a crucial factor influencing the static first hyperpolarizabilities for Tb1-Li and Tb2-Li. Furthermore, the βtot value of Tb1-Li is 6222 au, which is about 160 times larger than that of Tb1 (39 au). However, the βtot value of Tb2-Li (498 au) is only about 5 times larger than that of the corresponding Tb2 (91 au). It is our expectation that this work could provide useful information for the development of nonlinear optical materials based on carboranes.
Related Concept Videos
Directing and Steric Effects in Disubstituted Benzene Derivatives
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds
Stereoisomerism
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
NMR Spectroscopy of Benzene Derivatives

