TY - JOUR
T1 - Modulation of π-stacking modes and photophysical properties of an organic semiconductor through isosteric cocrystallization
AU - Campillo-Alvarado, Gonzalo
AU - Bernhardt, Michael
AU - Davies, Daniel W.
AU - Soares, Julio A.N.T.
AU - Woods, Toby J.
AU - Diao, Ying
N1 - Funding Information:
G.C.-A. acknowledges financial support from The Office for Access and Equity, the DRIVE Committee, and the Illinois Materials Research Center (University of Illinois at Urbana-Champaign) through the DRIVE Distinguished Postdoctoral Fellowship. Y.D. and D.W.D. acknowledge the Sloan Foundations for a Sloan Research Fellowship in Chemistry and a 3M Nontenured Faculty Award. This work was conducted, in part, in the George L. Clark X-Ray Facility and in the 3M Materials Laboratory and in the Materials Research Laboratory Central Research Facilities, University of Illinois. This research was partially supported by the NSF through the University of Illinois at Urbana-Champaign Materials Research Science and Engineering Center under Grant No. DMR-17-20633. The use of the Advanced Photon Source, an Office of Science User Facility operated for the U.S. Department of Energy (DOE) Office of Science by Argonne National Laboratory, was supported by the U.S. DOE under Contract No. DE-AC02-06CH11357. We are thankful to Dr. Danielle L. Gray (University of Illinois), Dr. Yu-Sheng Chen (ChemMatCARS), Dr. Tieyan Chang (ChemMat-CARS), Dr. Ying-Pin Chen (ChemMatCARS), and Dr. SuYin Grass Wang (ChemMatCARS) for assistance with SCXRD measurements. There are no conflicts of interest to declare.
Funding Information:
G.C.-A. acknowledges financial support from The Office for Access and Equity, the DRIVE Committee, and the Illinois Materials Research Center (University of Illinois at Urbana-Champaign) through the DRIVE Distinguished Postdoctoral Fellowship. Y.D. and D.W.D. acknowledge the Sloan Foundations for a Sloan Research Fellowship in Chemistry and a 3M Nontenured Faculty Award. This work was conducted, in part, in the George L. Clark X-Ray Facility and in the 3M Materials Laboratory and in the Materials Research Laboratory Central Research Facilities, University of Illinois. This research was partially supported by the NSF through the University of Illinois at Urbana-Champaign Materials Research Science and Engineering Center under Grant No. DMR-17-20633. The use of the Advanced Photon Source, an Office of Science User Facility operated for the U.S. Department of Energy (DOE) Office of Science by Argonne National Laboratory, was supported by the U.S. DOE under Contract No. DE-AC02-06CH11357. We are thankful to Dr. Danielle L. Gray (University of Illinois), Dr. Yu-Sheng Chen (ChemMatCARS), Dr. Tieyan Chang (ChemMatCARS), Dr. Ying-Pin Chen (ChemMatCARS), and Dr. SuYin Grass Wang (ChemMatCARS) for assistance with SCXRD measurements.
Publisher Copyright:
© 2021 Author(s).
PY - 2021/8/21
Y1 - 2021/8/21
N2 - We report on the control of π-stacking modes (herringbone vs slipped-stack) and photophysical properties of 9,10-bis((E)-2-(pyridin-4-yl)vinyl)anthracene (BP4VA), an anthracene-based organic semiconductor (OSC), by isosteric cocrystallization (i.e., the replacement of one functional group in a coformer with another of "similar"electronic structure) with 2,4,6-trihalophenols (3X-ph-OH, where X = Cl, Br, and I). Specifically, BP4VA organizes as slipped-stacks when cocrystallized with 3Cl-ph-OH and 3Br-ph-OH, while cocrystallization with 3I-ph-OH results in a herringbone mode. The photoluminescence and molecular frontier orbital energy levels of BP4VA were effectively modulated by the presence of 3X-ph-OH through cocrystallization. We envisage that the cocrystallization of OSCs with minimal changes in cocrystal formers can provide access to convenient structural and property diversification for advanced single-crystal electronics.
AB - We report on the control of π-stacking modes (herringbone vs slipped-stack) and photophysical properties of 9,10-bis((E)-2-(pyridin-4-yl)vinyl)anthracene (BP4VA), an anthracene-based organic semiconductor (OSC), by isosteric cocrystallization (i.e., the replacement of one functional group in a coformer with another of "similar"electronic structure) with 2,4,6-trihalophenols (3X-ph-OH, where X = Cl, Br, and I). Specifically, BP4VA organizes as slipped-stacks when cocrystallized with 3Cl-ph-OH and 3Br-ph-OH, while cocrystallization with 3I-ph-OH results in a herringbone mode. The photoluminescence and molecular frontier orbital energy levels of BP4VA were effectively modulated by the presence of 3X-ph-OH through cocrystallization. We envisage that the cocrystallization of OSCs with minimal changes in cocrystal formers can provide access to convenient structural and property diversification for advanced single-crystal electronics.
UR - https://www.scopus.com/pages/publications/85113488738
UR - https://www.scopus.com/pages/publications/85113488738#tab=citedBy
U2 - 10.1063/5.0059770
DO - 10.1063/5.0059770
M3 - Article
C2 - 34418924
SN - 0021-9606
VL - 155
JO - The Journal of Chemical Physics
JF - The Journal of Chemical Physics
IS - 7
M1 - 0059770
ER -