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Title: Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives

Abstract

Through a close examination of the intermolecular interactions of rubrene (1a) and select derivatives (1b–1p), a clearer understanding of why certain fluorinated rubrene derivatives pack with planar tetracene backbones has been achieved. In this study we synthesized, crystallized, and determined the packing structure of new rubrene derivatives (1h–p). Previously, we proposed that introducing electron-withdrawing CF3 substituents induced planarity by reducing intramolecular repulsion between the peripheral aryl groups (1e–g). However, we found that in most cases, further increasing the fluorine content of rubrene lead to twisted tetracene backbones in the solid state. To understand how rubrene (1a) and its derivatives (1b–p) pack in the solid state, we (re)examined the crystal structures through a systematic study of the close contacts. We found that planar tetracene cores occur when close contacts organize to produce an S symmetry element about a given rubrene molecule. Here, we report the first instance of rubrene derivatives (1l and 1n) that pack in a two-dimensional brick motif. The prospects for new rubrene derivatives in semiconductors were estimated by calculating the reorganization energies of the monomers and transfer integrals of the dimers we observed. Our work allows for the rational design and improved crystal engineering of new rubrene derivatives.

Authors:
 [1];  [1];  [1];  [1];  [1];  [1];  [1];  [1];  [1];  [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]
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  1. Univ. of Minnesota, Minneapolis, MN (United States)
Publication Date:
Research Org.:
Univ. of Minnesota, Minneapolis, MN (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; USDOE Office of Science (SC), Advanced Scientific Computing Research (ASCR). Scientific Discovery through Advanced Computing (SciDAC); National Science Foundation (NSF)
OSTI Identifier:
1534432
Grant/Contract Number:  
SC0008666; MRI-1229400
Resource Type:
Accepted Manuscript
Journal Name:
Crystal Growth and Design
Additional Journal Information:
Journal Volume: 17; Journal Issue: 2; Journal ID: ISSN 1528-7483
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; Chemistry; Crystallography; Materials science; Reaction products; Layered materials; Crystal structure; Oligomers; Molecular interactions

Citation Formats

Ogden, William A., Ghosh, Soumen, Bruzek, Matthew J., McGarry, Kathryn A., Balhorn, Luke, Young, Jr., Victor, Purvis, Lafe J., Wegwerth, Sarah E., Zhang, Zhuoran, Serratore, Nicholas A., Cramer, Christopher J., Gagliardi, Laura, and Douglas, Christopher J. Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives. United States: N. p., 2016. Web. doi:10.1021/acs.cgd.6b01497.
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Ogden, William A., Ghosh, Soumen, Bruzek, Matthew J., McGarry, Kathryn A., Balhorn, Luke, Young, Jr., Victor, Purvis, Lafe J., Wegwerth, Sarah E., Zhang, Zhuoran, Serratore, Nicholas A., Cramer, Christopher J., Gagliardi, Laura, & Douglas, Christopher J. Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives. United States. https://doi.org/10.1021/acs.cgd.6b01497
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Ogden, William A., Ghosh, Soumen, Bruzek, Matthew J., McGarry, Kathryn A., Balhorn, Luke, Young, Jr., Victor, Purvis, Lafe J., Wegwerth, Sarah E., Zhang, Zhuoran, Serratore, Nicholas A., Cramer, Christopher J., Gagliardi, Laura, and Douglas, Christopher J. Thu . "Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives". United States. https://doi.org/10.1021/acs.cgd.6b01497. https://www.osti.gov/servlets/purl/1534432.
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@article{osti_1534432,
title = {Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives},
author = {Ogden, William A. and Ghosh, Soumen and Bruzek, Matthew J. and McGarry, Kathryn A. and Balhorn, Luke and Young, Jr., Victor and Purvis, Lafe J. and Wegwerth, Sarah E. and Zhang, Zhuoran and Serratore, Nicholas A. and Cramer, Christopher J. and Gagliardi, Laura and Douglas, Christopher J.},
abstractNote = {Through a close examination of the intermolecular interactions of rubrene (1a) and select derivatives (1b–1p), a clearer understanding of why certain fluorinated rubrene derivatives pack with planar tetracene backbones has been achieved. In this study we synthesized, crystallized, and determined the packing structure of new rubrene derivatives (1h–p). Previously, we proposed that introducing electron-withdrawing CF3 substituents induced planarity by reducing intramolecular repulsion between the peripheral aryl groups (1e–g). However, we found that in most cases, further increasing the fluorine content of rubrene lead to twisted tetracene backbones in the solid state. To understand how rubrene (1a) and its derivatives (1b–p) pack in the solid state, we (re)examined the crystal structures through a systematic study of the close contacts. We found that planar tetracene cores occur when close contacts organize to produce an S symmetry element about a given rubrene molecule. Here, we report the first instance of rubrene derivatives (1l and 1n) that pack in a two-dimensional brick motif. The prospects for new rubrene derivatives in semiconductors were estimated by calculating the reorganization energies of the monomers and transfer integrals of the dimers we observed. Our work allows for the rational design and improved crystal engineering of new rubrene derivatives.},
doi = {10.1021/acs.cgd.6b01497},
journal = {Crystal Growth and Design},
number = 2,
volume = 17,
place = {United States},
year = {Thu Dec 29 00:00:00 EST 2016},
month = {Thu Dec 29 00:00:00 EST 2016}
}
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https://doi.org/10.1021/acs.cgd.6b01497
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Cited by: 20 works
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Figure 1 Figure 1: Rubrenes examined in this work.
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      Figures / Tables found in this record:

      Figure 1 (p. 5)figure
      Table 1 (p. 11)table
      Scheme 1 (p. 12)figure
      Figure 2 (p. 13)figure
      Table 2 (p. 15)table
      Figure 3 (p. 17)figure
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      Table 3 (p. 32)table
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      Table 4 (p. 37)table
      Figure 19 (p. 39)figure
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