Insight from electron density and energy framework analysis on the structural features of F                         x                         -TCNQ (x = 0, 2, 4) family of molecules

Rahul Shukla; Christian Ruzié; Guillaume Schweicher; Alan R. Kennedy; Yves H. Geerts; Deepak Chopra; Basab Chattopadhyay

doi:10.1107/S2052520618017109

Insight from electron density and energy framework analysis on the structural features of F _x -TCNQ (x = 0, 2, 4) family of molecules

Rahul Shukla, Christian Ruzié, Guillaume Schweicher, Alan R. Kennedy, Yves H. Geerts, Deepak Chopra, Basab Chattopadhyay

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

In this study, the nature and characteristics of the intramolecular and intermolecular interactions in crystal structures of the fluoro-substituted 7,7,8,8-tetracyanoquinodimethane (TCNQ) family of molecules, i.e. F _x -TCNQ (x = 0, 2, 4), are explored. The molecular geometry of the reported crystal structures is directly dependent on the degree of fluorination in the molecule, which consequently also results in the presence of an intramolecular N[triple-bond]C…F—C π-hole tetrel bond. Apart from this, the energy framework analysis performed along the respective transport planes provides new insights into the energetic distribution in this class of molecules.

Original language	English
Pages (from-to)	71-78
Number of pages	8
Journal	Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
Volume	75
Issue number	1
DOIs	https://doi.org/10.1107/S2052520618017109
State	Published - 1 Feb 2019
Externally published	Yes

Keywords

charge density analysis
electron density
energy framework
fluorination
intermolecular interactions
TCNQ
tetracyanoquinodimethane
tetrel bond
π-hole interaction

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Atomic and Molecular Physics, and Optics
Metals and Alloys
Materials Chemistry

Access to Document

10.1107/S2052520618017109

Cite this

Shukla, R., Ruzié, C., Schweicher, G., Kennedy, A. R., Geerts, Y. H., Chopra, D., & Chattopadhyay, B. (2019). Insight from electron density and energy framework analysis on the structural features of F _x -TCNQ (x = 0, 2, 4) family of molecules Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 75(1), 71-78. https://doi.org/10.1107/S2052520618017109

Shukla, Rahul ; Ruzié, Christian ; Schweicher, Guillaume ; Kennedy, Alan R. ; Geerts, Yves H. ; Chopra, Deepak ; Chattopadhyay, Basab. / Insight from electron density and energy framework analysis on the structural features of F _x -TCNQ (x = 0, 2, 4) family of molecules In: Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials. 2019 ; Vol. 75, No. 1. pp. 71-78.

@article{5ad7cad92bb7485e866602756cb79c24,

title = " Insight from electron density and energy framework analysis on the structural features of F x -TCNQ (x = 0, 2, 4) family of molecules ",

abstract = " In this study, the nature and characteristics of the intramolecular and intermolecular interactions in crystal structures of the fluoro-substituted 7,7,8,8-tetracyanoquinodimethane (TCNQ) family of molecules, i.e. F x -TCNQ (x = 0, 2, 4), are explored. The molecular geometry of the reported crystal structures is directly dependent on the degree of fluorination in the molecule, which consequently also results in the presence of an intramolecular N[triple-bond]C…F—C π-hole tetrel bond. Apart from this, the energy framework analysis performed along the respective transport planes provides new insights into the energetic distribution in this class of molecules. ",

keywords = "charge density analysis, electron density, energy framework, fluorination, intermolecular interactions, TCNQ, tetracyanoquinodimethane, tetrel bond, π-hole interaction",

author = "Rahul Shukla and Christian Ruzi{\'e} and Guillaume Schweicher and Kennedy, {Alan R.} and Geerts, {Yves H.} and Deepak Chopra and Basab Chattopadhyay",

note = "Funding Information: Funding for this research was provided by: Fonds De La Recherche Scientifique–FNRS (POLYGRAD Project 22333186 to Basab Chattopadhyay); DST-INSPIRE (award to Rahul Shukla); The Leverhulme Trust (Early Career Fellowship supported by the Isaac Newton Trust – award to Guillaume Schweicher). Publisher Copyright: {\textcopyright} International Union of Crystallography, 2019",

year = "2019",

month = feb,

day = "1",

doi = "10.1107/S2052520618017109",

language = "English",

volume = "75",

pages = "71--78",

journal = "Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials",

issn = "2052-5192",

publisher = "John Wiley and Sons Inc.",

number = "1",

}

Shukla, R, Ruzié, C, Schweicher, G, Kennedy, AR, Geerts, YH, Chopra, D & Chattopadhyay, B 2019, ' Insight from electron density and energy framework analysis on the structural features of F _x -TCNQ (x = 0, 2, 4) family of molecules ', Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, vol. 75, no. 1, pp. 71-78. https://doi.org/10.1107/S2052520618017109

Insight from electron density and energy framework analysis on the structural features of F _x -TCNQ (x = 0, 2, 4) family of molecules . / Shukla, Rahul; Ruzié, Christian; Schweicher, Guillaume; Kennedy, Alan R.; Geerts, Yves H.; Chopra, Deepak; Chattopadhyay, Basab.

In: Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, Vol. 75, No. 1, 01.02.2019, p. 71-78.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Insight from electron density and energy framework analysis on the structural features of F x -TCNQ (x = 0, 2, 4) family of molecules

AU - Shukla, Rahul

AU - Ruzié, Christian

AU - Schweicher, Guillaume

AU - Kennedy, Alan R.

AU - Geerts, Yves H.

AU - Chopra, Deepak

AU - Chattopadhyay, Basab

N1 - Funding Information: Funding for this research was provided by: Fonds De La Recherche Scientifique–FNRS (POLYGRAD Project 22333186 to Basab Chattopadhyay); DST-INSPIRE (award to Rahul Shukla); The Leverhulme Trust (Early Career Fellowship supported by the Isaac Newton Trust – award to Guillaume Schweicher). Publisher Copyright: © International Union of Crystallography, 2019

PY - 2019/2/1

Y1 - 2019/2/1

N2 - In this study, the nature and characteristics of the intramolecular and intermolecular interactions in crystal structures of the fluoro-substituted 7,7,8,8-tetracyanoquinodimethane (TCNQ) family of molecules, i.e. F x -TCNQ (x = 0, 2, 4), are explored. The molecular geometry of the reported crystal structures is directly dependent on the degree of fluorination in the molecule, which consequently also results in the presence of an intramolecular N[triple-bond]C…F—C π-hole tetrel bond. Apart from this, the energy framework analysis performed along the respective transport planes provides new insights into the energetic distribution in this class of molecules.

AB - In this study, the nature and characteristics of the intramolecular and intermolecular interactions in crystal structures of the fluoro-substituted 7,7,8,8-tetracyanoquinodimethane (TCNQ) family of molecules, i.e. F x -TCNQ (x = 0, 2, 4), are explored. The molecular geometry of the reported crystal structures is directly dependent on the degree of fluorination in the molecule, which consequently also results in the presence of an intramolecular N[triple-bond]C…F—C π-hole tetrel bond. Apart from this, the energy framework analysis performed along the respective transport planes provides new insights into the energetic distribution in this class of molecules.

KW - charge density analysis

KW - electron density

KW - energy framework

KW - fluorination

KW - intermolecular interactions

KW - TCNQ

KW - tetracyanoquinodimethane

KW - tetrel bond

KW - π-hole interaction

UR - http://www.scopus.com/inward/record.url?scp=85061331668&partnerID=8YFLogxK

U2 - 10.1107/S2052520618017109

DO - 10.1107/S2052520618017109

M3 - Article

C2 - 32830780

AN - SCOPUS:85061331668

VL - 75

SP - 71

EP - 78

JO - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

JF - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

SN - 2052-5192

IS - 1

ER -

Shukla R, Ruzié C, Schweicher G, Kennedy AR, Geerts YH, Chopra D et al. Insight from electron density and energy framework analysis on the structural features of F _x -TCNQ (x = 0, 2, 4) family of molecules Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials. 2019 Feb 1;75(1):71-78. https://doi.org/10.1107/S2052520618017109