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

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

5 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

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Publisher Copyright:
© 2016 American Chemical Society.

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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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.}",

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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.

PY - 2016/4/6

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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.

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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

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