Parallel and Perpendicular Packing in Mixed-Stack Cocrystals of Trimeric Perfluoro-ortho-phenylene Mercury and Benzo[1,2-b:6,5-b′]dithiophene-4,5-dione Derivatives

Raúl Castañeda; Marina S. Fonari; Chad Risko; Yulia A. Getmanenko; Tatiana V. Timofeeva

doi:10.1021/acs.cgd.6b00001

Parallel and Perpendicular Packing in Mixed-Stack Cocrystals of Trimeric Perfluoro-ortho-phenylene Mercury and Benzo[1,2-b:6,5-b′]dithiophene-4,5-dione Derivatives

Raúl Castañeda, Marina S. Fonari, Chad Risko, Yulia A. Getmanenko, Tatiana V. Timofeeva

Chemistry

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

3 Scopus citations

Abstract

Seven cocrystals derived from 2,7-substituted benzo[1,2-b:6,5-b′]dithiophene-4,5-diones (BDDO) and trimeric perfluoro-o-phenylene mercury (TPPM) exhibit two prominent packing motifs: parallel mixed stacks and T-shaped columnar structures. The varied packing patterns reveal an interplay of noncovalent intermolecular interactions that depend on the nature of the BDDO 2,7-substituents and on the crystallization conditions. Quantum-chemical analyses show little charge-transfer character in the mixed-stack structures, suggesting limited electronic interaction among the mixed TPPM and BDDO constituents. The variations in molecular packing with rather minimal change in chemical structure expose the ability to fine-tune the structure of these molecular cocrystals.

Original language	English
Pages (from-to)	2190-2200
Number of pages	11
Journal	Crystal Growth and Design
Volume	16
Issue number	4
DOIs	https://doi.org/10.1021/acs.cgd.6b00001
State	Published - Apr 6 2016

Bibliographical note

Funding Information:
The authors are grateful for NSF support via DMR-0934212 and DMR-1523611 (PREM) and IIA-130134. C.R. thanks the University of Kentucky Vice President for Research for start-up funds. Benzo[1,2-b:6,5-b']dithiophene-4,5-dione derivatives were synthesized by Y.A.G. in the lab of Professor Seth R. Marder, who is acknowledged for providing these materials for the study. Y.A.G. thanks Dr. Kyril Solntsev for support. R.C. thanks the instructors of the American Crystallographic Asociation summer course for assistance in the refining of three structures.

Publisher Copyright:
© 2016 American Chemical Society.

ASJC Scopus subject areas

Chemistry (all)
Materials Science (all)
Condensed Matter Physics

Access to Document

10.1021/acs.cgd.6b00001

Cite this

@article{ac3d177aa44c44abab069965b815ec79,

title = "Parallel and Perpendicular Packing in Mixed-Stack Cocrystals of Trimeric Perfluoro-ortho-phenylene Mercury and Benzo[1,2-b:6,5-b′]dithiophene-4,5-dione Derivatives",

abstract = "Seven cocrystals derived from 2,7-substituted benzo[1,2-b:6,5-b′]dithiophene-4,5-diones (BDDO) and trimeric perfluoro-o-phenylene mercury (TPPM) exhibit two prominent packing motifs: parallel mixed stacks and T-shaped columnar structures. The varied packing patterns reveal an interplay of noncovalent intermolecular interactions that depend on the nature of the BDDO 2,7-substituents and on the crystallization conditions. Quantum-chemical analyses show little charge-transfer character in the mixed-stack structures, suggesting limited electronic interaction among the mixed TPPM and BDDO constituents. The variations in molecular packing with rather minimal change in chemical structure expose the ability to fine-tune the structure of these molecular cocrystals.",

author = "Ra{\'u}l Casta{\~n}eda and Fonari, {Marina S.} and Chad Risko and Getmanenko, {Yulia A.} and Timofeeva, {Tatiana V.}",

note = "Funding Information: The authors are grateful for NSF support via DMR-0934212 and DMR-1523611 (PREM) and IIA-130134. C.R. thanks the University of Kentucky Vice President for Research for start-up funds. Benzo[1,2-b:6,5-b']dithiophene-4,5-dione derivatives were synthesized by Y.A.G. in the lab of Professor Seth R. Marder, who is acknowledged for providing these materials for the study. Y.A.G. thanks Dr. Kyril Solntsev for support. R.C. thanks the instructors of the American Crystallographic Asociation summer course for assistance in the refining of three structures. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = apr,

day = "6",

doi = "10.1021/acs.cgd.6b00001",

language = "English",

volume = "16",

pages = "2190--2200",

number = "4",

}

TY - JOUR

T1 - Parallel and Perpendicular Packing in Mixed-Stack Cocrystals of Trimeric Perfluoro-ortho-phenylene Mercury and Benzo[1,2-b:6,5-b′]dithiophene-4,5-dione Derivatives

AU - Castañeda, Raúl

AU - Fonari, Marina S.

AU - Risko, Chad

AU - Getmanenko, Yulia A.

AU - Timofeeva, Tatiana V.

N1 - Funding Information: The authors are grateful for NSF support via DMR-0934212 and DMR-1523611 (PREM) and IIA-130134. C.R. thanks the University of Kentucky Vice President for Research for start-up funds. Benzo[1,2-b:6,5-b']dithiophene-4,5-dione derivatives were synthesized by Y.A.G. in the lab of Professor Seth R. Marder, who is acknowledged for providing these materials for the study. Y.A.G. thanks Dr. Kyril Solntsev for support. R.C. thanks the instructors of the American Crystallographic Asociation summer course for assistance in the refining of three structures. Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/4/6

Y1 - 2016/4/6

N2 - Seven cocrystals derived from 2,7-substituted benzo[1,2-b:6,5-b′]dithiophene-4,5-diones (BDDO) and trimeric perfluoro-o-phenylene mercury (TPPM) exhibit two prominent packing motifs: parallel mixed stacks and T-shaped columnar structures. The varied packing patterns reveal an interplay of noncovalent intermolecular interactions that depend on the nature of the BDDO 2,7-substituents and on the crystallization conditions. Quantum-chemical analyses show little charge-transfer character in the mixed-stack structures, suggesting limited electronic interaction among the mixed TPPM and BDDO constituents. The variations in molecular packing with rather minimal change in chemical structure expose the ability to fine-tune the structure of these molecular cocrystals.

AB - Seven cocrystals derived from 2,7-substituted benzo[1,2-b:6,5-b′]dithiophene-4,5-diones (BDDO) and trimeric perfluoro-o-phenylene mercury (TPPM) exhibit two prominent packing motifs: parallel mixed stacks and T-shaped columnar structures. The varied packing patterns reveal an interplay of noncovalent intermolecular interactions that depend on the nature of the BDDO 2,7-substituents and on the crystallization conditions. Quantum-chemical analyses show little charge-transfer character in the mixed-stack structures, suggesting limited electronic interaction among the mixed TPPM and BDDO constituents. The variations in molecular packing with rather minimal change in chemical structure expose the ability to fine-tune the structure of these molecular cocrystals.

UR - http://www.scopus.com/inward/record.url?scp=84964579701&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84964579701&partnerID=8YFLogxK

U2 - 10.1021/acs.cgd.6b00001

DO - 10.1021/acs.cgd.6b00001

M3 - Article

AN - SCOPUS:84964579701

SN - 1528-7483

VL - 16

SP - 2190

EP - 2200

JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 4

ER -

Parallel and Perpendicular Packing in Mixed-Stack Cocrystals of Trimeric Perfluoro-ortho-phenylene Mercury and Benzo[1,2-b:6,5-b′]dithiophene-4,5-dione Derivatives

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this