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Study of Intermolecular Interaction of HO-(CH2)n-O-C6H4-C6H4-CN

(HnCBP) Liquid Crystals molecule by using DFT methods

Arvind Kumar Dwivedi1, Deep Kumar2, and Jitendra Kumar3*

1Department of Physics, M.L.K.(PG) College Balrampur-271201, U.P.,India

2Department of Basic Science, Babasaheb Bhimrao Ambedkar University,

Lucknow- 226 025, U.P., India

3*Department of Physics, Babasaheb Bhimrao Ambedkar University, Lucknow- 226 025, U.P.,

India [email protected], [email protected], 3*[email protected]

Abstract

Characteristic properties of liquid crystals molecule have been explained by using the pairs of

molecules. The staking interaction energy explains the liquid crystalline behaviour of the system. The

homologous structure (HnCBP) has been optimized using the density functional theory (DFT) B3LYP

Hybrid function with 6-31G basis set using the crystallographic geometry as input. Is used molecular

interaction is found to play a significant role in the formation of mesophase and also the stability of the

liquid crystal molecule. Stability of their mesogenic phase has been of interest since long and it is well

established now that mesogenic property of a compound is due to asymmetry intermolecular interaction

of a pair of molecule.

Keywords: DFT, B3LYP, Interaction, Liquid crystal, Stacking

Introduction

The study of relationship between molecular structure of liquid crystal compounds and stability

of their mesogenic phase has been of interest since long and it is well established now that

mesogenic property of a compound is due to asymmetry intermolecular interaction of a pair of

molecule [1, 2]. The study on the effect of physiochemical properties of 2, 5-disubstituted

pyridine derivatives liquid crystal molecules by introducing the fragment of pyridine 2, 5-diyl

into the molecular core have drawn attention of several scientists working in this field [3-13]. C.

G Le Fevre, and R. J. W Le Fevre [14] have reviewed about pyridine derivative molecule and

established some peculiar structure - mesogenic property relationships. It is interesting to note

that the change in alkyl chain length or variation of position of hetro atom in the pyridines

derivatives having two ring alkyl and alkoxyl group affect the mesogenic properties significantly

[14]. The number of nitrogen atom and its position in pyridine ring for 2,5-disubstituted pyridine

derivatives plays an important role on mesomorphic properties of these molecules. It was also

observed that the structure, geometrical and electronic, of the pyridine ring [15-18] also

influence the mesophase stability [19-21].

Journal of Information and Computational Science

Volume 9 Issue 7 - 2019

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mailto:[email protected]

Although several model were proposed to understand the behavior of materials with respect to

intermolecular association energy for a pair of molecule as discussed in chapter-I but in early

1980s, Tokita et al. [22] first time tried to correlate the behavior of materials with the

intermolecular association energy through quantitative evaluation from actual molecular

structure. They estimated the variation of intermolecular interaction energy for nematic liquid

crystal molecule by changing the relative orientation of the interacting pair of molecule and the

obtained results are in good agreement with the Maier-Saupe model. The estimated association

energy for a pair of molecule indicated the strong tendency of the molecular alignment along the

long molecular axis. Sanyal et al. [23-27] also obtained the similar results for a number of

nematogens, by taking account of intermolecular interaction from the actual molecular structure.

They also tried to estimate the intermolecular association energy for stacking interaction, in-

plane interaction and terminal interactions for a pair of several mesogenic molecules. Although

studies started were further extended to correlate the total intermolecular interaction energy with

transition temperature [28, 29]. Major problem for these studies is that it uses classical equation

for estimation of pair potential in which atomic charges and atomic dipoles were computed from

the crystal structure using CNDO/2 semiempirical method. Later, Roychoudhury et al. [30]

started optimizing molecular structure using DFT (B3LYP) method with 6-31G** basis sets.

They use to compute intermolecular interaction energy using atomic charges and atomic dipoles

obtained from DFT calculations. The minimum energy configurations for all type of possible

interactions were again optimized with some constraints using B3LYP and obtained the

improved results.

Hence, it was decided to use DFT method to optimize the molecular structure as well as

interacting pair without any constraint to estimate the pair potential quantum mechanically. For

this study, the system chosen is biphenyl derivatives with polar group on both terminal ends and

also belongs to a highly studied class of liquid crystal compound. The chosen homologous series

has the general form HO-(CH2)n-O-C6H4-C6H4-CN (HnCBP) for n = 3-11 and all molecules of

this series exist in nematic phase [31, 32]. This present study will help to design new type of

liquid crystals with improved properties.

Method of calculation

DFT calculations for HnCBP and its derivatives were performed. A uniform strategy is adopted

for the study of these molecules. The molecular structures were generated based on crystal

structure available in literature [31, 32] using Gauss view program suite. The geometry

optimization has been carried out without any constraints and also analytical frequency

calculation were performed to check the imaginary frequencies, if any, using UCAM-B3LYP

[33] method with 6-31G** [34] basis set. From the optimized geometry, stacked pair of

molecules were also generated with the scheme shown in figure 6.1 using Gauss View program

suite. The geometry of stacked pairs were optimized and also checked for imaginary frequency

using UCAM-B3LYP with 6-31G** basis. The CAM-B3LYP method is improved version of



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B3LYP which also account for long range interaction. The geometry optimization and analytical

frequency calculations were performed using Gaussian 09 program suite [35].

Figure 1: The scheme for mode of stacking interaction of molecular pair. (S1 represent side A

and S2 represent side B of molecular face).

Result and Discussion

The optimized geometry as well as optimized stacked pair of HnCBP molecules for n= 3–11 are

presented in figure 2.

Z

Y

X

S

S P

P



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Figure 2(a): The optimized geometry of H3CBP molecule and its stacked pair.



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Figure 2(b):The optimized geometry of H4CBP molecule and its stacked pair.



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Figure 2(c):The optimized geometry of H5CBP molecule and its stacked pair.



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Figure 2(d):The optimized geometry of H6CBP molecule and its stacked pair.



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Figure 2(e):The optimized geometry of H7CBP molecule and its stacked pair.



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Figure 2(f):The optimized geometry of H8CBP molecule and its stacked pair.



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Figure 2(g):The optimized geometry of H9CBP molecule and its stacked pair.



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Figure 2(h):The optimized geometry of H10CBP molecule and its stacked pair.



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Figure 2(i):The optimized geometry of H11CBP molecule and its stacked pair.



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Table 1: The total energy of individual HnCBP molecules, total energy of stacking side A and

side B, intermolecular interaction energy for stacking side A, side B and total

interaction energy for HnCBP molecules.

Total Energy

(hartree)

Intermolecular

Interaction

Energy (kcal/mol)

Molecule Individual

Molecule

Stacking

Side A

Stacking

Side B

Side A

Side B

Total

H3CBP -823.250054 -1646.509139 -1646.520325 -5.66 -12.68 -18.35

H4CBP -862.525377 -1725.063898 -1725.067225 -8.25 -10.33 -18.58

H5CBP -901.803950 -1803.619262 -1803.620665 -7.12 -8.01 -15.14

H6CBP -941.083582 -1882.176360 -1882.177593 -5.77 -6.54 -12.31

H7CBP -980.361377 -1960.730939 -1960.746416 -5.13 -14.84 -25.12

H8CBP -1019.640712 -2039.290853 -2039.288208 -5.91 -4.25 -10.17

H09CBP -1058.918628 -2117.856252 -2117.854194 -11.91 -10.62 -22.54

H10CBP -1098.197845 -2196.405188 -2196.418731 -5.96 -14.45 -20.41

H11CBP -1137.475830 -2274.960262 -2274.961507 -5.39 -6.17 -11.57

Table 1 presents the total energy of individual HnCBP molecules, total energy of stacking side A

and side B, intermolecular interaction energy for stacking side A, side B and total interaction

energy for HnCBP molecules. From the table, it is evident that pair potentials for the stacking

side A and the stacking side B interactions are asymmetrical for all molecules of the HnCBP

series.

For H3CBP molecule, CN group of one molecule interacts with alkoxy group of another

molecule in stacking side A interaction. In stacking side B interaction there is OH---OH

hydrogen bond at one end of molecular alignment whereas CN group of one molecule interact

with benzene ring of another molecule (figure 2(a)) that results in lowers the interaction energy

of side B than that of side A.

For H4CBP molecule, in stacking side A interaction both molecules interact with each other in

opposite orientation The OH Group of one molecule interacts with benzene ring of another

molecule. In case of stacking side B interaction both molecules interact in parallel fashion with

same orientation, therefore, there is HO---HO interaction at one end and CN Group interaction at

another end (figure 2(b)). Since polar groups interaction for both side of stacking interaction

exibiting almost similar interacting energy is almost similar.

For H5CBP molecule, in stacking side A interaction both molecules interact each other is

opposite orientation. In this case, biphenyl rings of both molecules interact with each other. In

stacking side B interaction both molecule interact with each other with is orientation. The alkoxy

group with extended alkyl chain of one molecule interact with biphenyl group of the second



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molecule and CN group of second molecule interacts with benzene ring of first molecule (figure

2(c)). The interaction energy in both cases is similar but higher than that of H4CBP molecule.

For H6CBP molecule, in stacking side A interaction, opposite oriented molecules interacts

faceing of each other. The alkoxy and alkyl chain of each molecule interact with biphenyl ring of

each other. In stacking side B interaction, molecules interact with each other in same orientation.

The CN group and adjacent benzene ring of one molecule interacts with outer benzene ring of

the second molecule and inner benzene ring, alkoxy chain interacts with inner benzene ring,

alkoxy chain of first molecule (figure 2(d)). Because of interaction of CN group with benzene

ring, the interaction energy of stacking side B is slightly lower than that of stacking side A. The

interaction energy of both sides is higher than that of H5CBP molecule.

For H7CBP molecule, the stacking side A interaction follows the same pattern that of H6CBP

molecule, thereby the interaction energy is also similar. The stacking side B interaction also as

the similar pattern of interaction for of H6CBP molecule but there is OH---OH hydrogen

bonding interaction (figure 2 (e)) which lowers the interaction energy, thereby total interaction

energy for H7CBP molecule is lower than that of H6CBP molecule.

For H8CBP molecule, in stacking side A, the biphenyl rings interact with alkoxy chain of the

molecules oriented opposite to each other and in stacking side B, the interacting molecules have

the same orientation and the CN group of one molecule interact with benzene ring of another

molecule (figure 2 (f)). Due to the interaction of polar group with benzene ring, the interaction

energy for side B is lower than that of side A.

For H9CBP molecule, in stacking side A, there is OH---CN group hydrogen bonding pattern at

both terminal ends for oppositely oriented interacting molecules whereas in stacking side B,

there is OH---OH hydrogen bonding as well as interaction between the CN group of one

molecule with benzene ring of second molecule (figure 2 (g)) in the interacting molecules with

same orientation. Hence, interaction energy of both sides is similar.

For H10CBP molecule, there is interaction between long alkoxy chain of each molecule for

stacking side A and in stacking side B interaction there is CN---OH hydrogen bonding at the

both ends of oppositely oriented interacting molecules (figure 2 (h)), thereby interaction energy

of stacking side B is much lower than that of stacking side A.

For H11CBP molecules, there is interaction between biphenyl rings with long alkoxy chain, the

molecules are oriented oppositely in stacking side A and the molecules are in same orientation in

stacking side B. The interaction energy for stacking side B is lower than that of stacking side B

(figure 2 (i)).

Table 2: The dipole moment for HnCBP molecules for n = 3 – 11.

Molecules Dipole Moment (debye)

Individual Stacking Side A Stacking Side B

H3CBP 6.49 0.10 11.34

H4CBP 5.02 0.04 11.68

H5CBP 6.67 0.06 13.12



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H6CBP 8.11 0.12 15.71

H7CBP 6.71 0.30 15.54

H8CBP 8.13 0.05 15.94

H9CBP 6.74 0.01 14.30

H10CBP 8.13 16.88 4.43

H11CBP 6.76 0.03 13.67

Table 2 presents the dipole moment of individual molecule, stacking side A, stacking side B of

HnCBP molecules for n = 3 – 11. From the table it clear that the dipole moment of interacting

pair of molecules are close to zero if molecule interact symmetrically and the dipole moment is

higher than individual molecule if interaction is not symmetrical. The stacking side A interaction

are symmetrical for all molecules of HnCBP series except H10CBP. The stacking side B

interaction for all molecules of the series are asymmetrical except H10CBP. In case of H10CBP

molecule the stacking side A interaction is asymmetrical and the stacking side B interaction is

close to symmetrical interaction.

Conclusion

The intermolecular interaction for pair of molecules of HnCBP homologous series were

calculated using CAM-B3LYP method. The interaction energies for the stacking side A and the

stacking side B of molecules were found asymmetrical.

Acknowledgments

Author thanks of gratitude to Prof. Devesh Kumar Department of Physics, Babasaheb Bhimrao

Ambedkar University, Lucknow, He provide me computer lab and necessary facility of this

work. Which also helped me in doing a lot of Research work.

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