Comparative analysis on all di-chlorostyrenes; a DFT-B3LYP study

The use of electrically conducting polymers in electro-chromic devices, as materials that possess the ability to reversibly change color by altering redox state, has emerged. Many conjugated polymers are colored in the neutral state since the energy difference between the σ-bonding orbitals and the σ* anti-bonding orbitals (valence band) lies within the visible region [1]. The conductivity study and the electrochemical polymerization of conducting compounds (or monomers) is an interesting matter for Scientifics in the world. Electrically conducting polymers have been considered for numerous applications including charge dissipation coatings, organic thin-film transistors, and conducting textiles. All of the possible of dichlorostyrenes studied in this work are presented in Fig. 1. 1: Z=W=X=T=R=Q=L=H Styrene 2: Z=W=R=Q=L=H,X=T=Cl 1,2-dichloro-3-vinylbenzene 3: Z=W=T=Q=L=H,X=R=Cl 2,4-dichloro-1-vinylbenzene 4: Z=W=T=R=L=H,X=Q=Cl 1,4-dichloro-2-vinylbenzene 5: Z=W=T=R=Q=H,X=L=Cl 1,3-dichloro-2-vinylbenzene6: Z=W=X=T=R=H,Q=L=Cl (Z)-1,2-dichloro-3-vinylbenzene 7: Z=W=X=T=Q=H,L=R=Cl (Z)-2,4-dichloro-1-vinylbenzene 8: Z=W=X=R=Q=H,L=T=Cl (Z)-1,4-dichloro-2-vinylbenzene9: Z=W=X=R=L=H,Q=T=Cl 1,3-dichloro-5-vinylbenzene 10: Z=W=X=T=L=H,Q=R=Cl 1,2-dichloro-4-vinylbenzene 11: Z=W=X=Q=L=H,T=R=Cl (Z)-1,2-dichloro-4-vinylbenzene12: Z=T=R=Q=L=H,W=X=Cl 1-chloro-2-(1-chlorovinyl)benzene 13: Z=X=R=Q=L=H,W=T=Cl 1-chloro-3-(1-chlorovinyl)benzene 14: Z=X=T=Q=L=H,W=R=Cl 1-chloro-4-(1-chlorovinyl)benzene 15: Z=X=T=R=L=H,W=Q=Cl (Z)-1-chloro-3-(1-chlorovinyl)benzene 16: Z=X=T=R=Q=H,W=L=Cl (Z)-1-chloro-2-(1-chlorovinyl)benzene 17: X=T=R=Q=L=H,W=Z=Cl 1-(1,2-dichlorovinyl)benzene 18: W=T=R=Q=L=H,Z=X=Cl 1-chloro-2-(2-chlorovinyl)benzene 19: W=X=R=Q=L=H,Z=T=Cl 1-chloro-3-(2-chlorovinyl)benzene 20: W=X=T=Q=L=H,Z=R=Cl 1-chloro-4-(2-chlorovinyl)benzene 21: W=X=T=R=L=H,Z=Q=Cl (Z)-1-chloro-3-(2-chlorovinyl)benzene Fig. 1 All di-chlorostyrenes studied in this work.The structural and electrical properties of all di-chlorostyrenes have been studied using B3LYP method with 6-311++G basis set. Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) energies, HLG (the gap between HOMO and LUMO) and size of dipole moment vector, total electrical energies, enthalpies, entropies, electronic, Gibbs and Zero-Point energies, and also IR spectra have been calculated and studied in this work. The analysis of these data showed that the 1-chloro-4-(2-chlorovinyl)benzene has the highest value of the dipole moment (i.e. 2.9696 D). The analysis of data showed that the 1-chloro-3-(2- chlorovinyl)benzene has the lowest HLG and highest delocalization double bonds.