Exploring the structural changes on excitation of a luminescent organic bromine-substituted complex by in-house time-resolved pump-probe diffraction

Basuroy, Krishnayan; Chen, Yang; Sarkar, Sounak; Benedict, Jason; Coppens, Philip

doi:10.1063/1.4978240

Title: Exploring the structural changes on excitation of a luminescent organic bromine-substituted complex by in-house time-resolved pump-probe diffraction

Journal Article · 09 March 2017 · Structural Dynamics

DOI: https://doi.org/10.1063/1.4978240 · OSTI ID:1393450

Basuroy, Krishnayan ^[1]; Chen, Yang ^[1]; Sarkar, Sounak ^[1]; Benedict, Jason ^[1]; Coppens, Philip ^[1]

State Univ. of New York (SUNY), Buffalo, NY (United States). Dept. of Chemistry

The structural changes accompanying the excitation of the luminescent dibromobenzene derivative, 1,4-dibromo-2,5-bis(octyloxy)benzene, have been measured by in-house monochromatic time-resolved (TR) diffraction at 90 K. Results show an increment of the very short intermolecular Br•••Br contact distance from 3.290 Å to 3.380 Å. These calculations show the Br…Br interaction to be strongly repulsive in both the Ground and Excited states but significantly relaxed by the lengthening of the contact distance on excitation. The stability of the crystals is attributed to the many weak C-H···Br and C-H···π intermolecular interactions. Our study described is the first practical application of In-House Time-Resolved diffraction, made possible by the continuing increase in the brightness of X-ray sources and the sensitivity of our detectors.

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Research Organization:: State Univ. of New York (SUNY), Buffalo, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: FG02-02ER15372

OSTI ID:: 1393450

Journal Information:: Structural Dynamics, Vol. 4, Issue 2; ISSN 2329-7778

Publisher:: American Crystallographic Association/AIPCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 6 works

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References (57)

Can short-range hybrids describe long-range-dependent properties? Henderson, Thomas M.; Izmaylov, Artur F.; Scalmani, Giovanni The Journal of Chemical Physics, Vol. 131, Issue 4 https://doi.org/10.1063/1.3185673	journal	July 2009
Selective time-dependent changes of Cu(DPPE)(DMP)·PF ₆ on photoexcitation Trzop, Elzbieta; Fournier, Bertrand; Jarzembska, Katarzyna Acta Crystallographica Section A Foundations and Advances, Vol. 70, Issue a1 https://doi.org/10.1107/S2053273314092237	journal	August 2014
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Efficient hybrid density functional calculations in solids: Assessment of the Heyd–Scuseria–Ernzerhof screened Coulomb hybrid functional Heyd, Jochen; Scuseria, Gustavo E. The Journal of Chemical Physics, Vol. 121, Issue 3, p. 1187-1192 https://doi.org/10.1063/1.1760074	journal	July 2004
Recent advances in purely organic phosphorescent materials Mukherjee, Sanjoy; Thilagar, Pakkirisamy Chemical Communications, Vol. 51, Issue 55 https://doi.org/10.1039/C5CC03114A	journal	January 2015
Data scaling and temperature calibration in time-resolved photocrystallographic experiments Schmøkel, Mette S.; Kamiński, Radosław; Benedict, Jason B. Acta Crystallographica Section A Foundations of Crystallography, Vol. 66, Issue 6 https://doi.org/10.1107/S0108767310029429	journal	September 2010
An empirical correction for absorption anisotropy Blessing, R. H. Acta Crystallographica Section A Foundations of Crystallography, Vol. 51, Issue 1 https://doi.org/10.1107/S0108767394005726	journal	January 1995
Efficient computer modeling of organic materials. The atom–atom, Coulomb–London–Pauli (AA-CLP) model for intermolecular electrostatic-polarization, dispersion and repulsion energies Gavezzotti, Angelo New Journal of Chemistry, Vol. 35, Issue 7 https://doi.org/10.1039/c0nj00982b	journal	January 2011
Unexpected “amphoteric” character of the halogen bond: the charge density study of the co-crystal of N-methylpyrazine iodide with I2 Nelyubina, Yulia V.; Antipin, Mikhail Yu.; Dunin, Dmitriy S. Chemical Communications, Vol. 46, Issue 29 https://doi.org/10.1039/c0cc01094d	journal	January 2010
Extension of Gaussian‐2 theory to molecules containing third‐row atoms Ga–Kr Curtiss, Larry A.; McGrath, Mark P.; Blaudeau, Jean‐Philippe The Journal of Chemical Physics, Vol. 103, Issue 14 https://doi.org/10.1063/1.470438	journal	October 1995
Enhancing Organic Phosphorescence by Manipulating Heavy-Atom Interaction Shi, Huifang; An, Zhongfu; Li, Pei-Zhou Crystal Growth & Design, Vol. 16, Issue 2 https://doi.org/10.1021/acs.cgd.5b01400	journal	January 2016
Outlier Treatment in Data Merging Blessing, R. H. Journal of Applied Crystallography, Vol. 30, Issue 4 https://doi.org/10.1107/S0021889896014628	journal	August 1997
Energy band gaps and lattice parameters evaluated with the Heyd-Scuseria-Ernzerhof screened hybrid functional Heyd, Jochen; Peralta, Juan E.; Scuseria, Gustavo E. The Journal of Chemical Physics, Vol. 123, Issue 17 https://doi.org/10.1063/1.2085170	journal	November 2005
Influence of the exchange screening parameter on the performance of screened hybrid functionals Krukau, Aliaksandr V.; Vydrov, Oleg A.; Izmaylov, Artur F. The Journal of Chemical Physics, Vol. 125, Issue 22 https://doi.org/10.1063/1.2404663	journal	December 2006
Achieving Persistent Room Temperature Phosphorescence and Remarkable Mechanochromism from Pure Organic Luminogens Gong, Yongyang; Chen, Gan; Peng, Qian Advanced Materials, Vol. 27, Issue 40 https://doi.org/10.1002/adma.201502442	journal	September 2015
On the assessment of time-resolved diffraction results Fournier, Bertrand; Coppens, Philip Acta Crystallographica Section A Foundations and Advances, Vol. 70, Issue 3 https://doi.org/10.1107/S2053273314006305	journal	May 2014
Efficient evaluation of short-range Hartree-Fock exchange in large molecules and periodic systems Izmaylov, Artur F.; Scuseria, Gustavo E.; Frisch, Michael J. The Journal of Chemical Physics, Vol. 125, Issue 10 https://doi.org/10.1063/1.2347713	journal	September 2006
On the Analysis of Reversible Light-Induced Changes in Molecular Crystals Ozawa, Y.; Pressprich, M. R.; Coppens, P. Journal of Applied Crystallography, Vol. 31, Issue 2 https://doi.org/10.1107/S0021889897007802	journal	April 1998
Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg Hay, P. Jeffrey; Wadt, Willard R. The Journal of Chemical Physics, Vol. 82, Issue 1 https://doi.org/10.1063/1.448799	journal	January 1985
Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals Hay, P. Jeffrey; Wadt, Willard R. The Journal of Chemical Physics, Vol. 82, Issue 1, p. 299-310 https://doi.org/10.1063/1.448975	journal	January 1985
Shedding Light on the Photochemistry of Coinage-Metal Phosphorescent Materials: A Time-Resolved Laue Diffraction Study of an Ag ^I –Cu ^I Tetranuclear Complex Jarzembska, Katarzyna N.; Kamiński, Radosław; Fournier, Bertrand Inorganic Chemistry, Vol. 53, Issue 19 https://doi.org/10.1021/ic501696y	journal	September 2014
Toward reliable density functional methods without adjustable parameters: The PBE0 model Adamo, Carlo; Barone, Vincenzo The Journal of Chemical Physics, Vol. 110, Issue 13 https://doi.org/10.1063/1.478522	journal	April 1999
The nature of halogen.cntdot..cntdot..cntdot.halogen interactions: are short halogen contacts due to specific attractive forces or due to close packing of nonspherical atoms? Desiraju, Gautam R.; Parthasarathy, R. Journal of the American Chemical Society, Vol. 111, Issue 23 https://doi.org/10.1021/ja00205a027	journal	November 1989
Data Reduction and Error Analysis for Accurate Single Crystal Diffraction Intensities Blessing, Robert H. Crystallography Reviews, Vol. 1, Issue 1 https://doi.org/10.1080/08893118708081678	journal	January 1987
Nature of Cl···Cl Intermolecular Interactions via Experimental and Theoretical Charge Density Analysis: Correlation of Polar Flattening Effects with Geometry Hathwar, Venkatesha R.; Row, Tayur N. Guru The Journal of Physical Chemistry A, Vol. 114, Issue 51 https://doi.org/10.1021/jp1100413	journal	December 2010
Stabilizing triplet excited states for ultralong organic phosphorescence An, Zhongfu; Zheng, Chao; Tao, Ye Nature Materials, Vol. 14, Issue 7 https://doi.org/10.1038/nmat4259	journal	April 2015
Assessment and validation of a screened Coulomb hybrid density functional Heyd, Jochen; Scuseria, Gustavo E. The Journal of Chemical Physics, Vol. 120, Issue 16 https://doi.org/10.1063/1.1668634	journal	April 2004
Transferability of nonbonded Cl...Cl potential energy function to crystalline chlorine Williams, D. E.; Hsu, L. -Y. Acta Crystallographica Section A Foundations of Crystallography, Vol. 41, Issue 3 https://doi.org/10.1107/S0108767385000630	journal	May 1985
Crystal Structure of 2,3,6,7-Tetrabromo-9,10-dihydro-9,10-ethanoanthracene Kitamura, Chitoshi; Hasegawa, Takayuki; Kawatsuki, Nobuhiro Analytical Sciences: X-ray Structure Analysis Online, Vol. 23 https://doi.org/10.2116/analscix.23.x207	journal	January 2007
LASER – a program for response-ratio refinement of time-resolved diffraction data Vorontsov, Ivan; Pillet, Sébastien; Kamiński, Radosław Journal of Applied Crystallography, Vol. 43, Issue 5 https://doi.org/10.1107/S0021889810029900	journal	August 2010
The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors Boys, S.F.; Bernardi, F. Molecular Physics, Vol. 19, Issue 4, p. 553-566 https://doi.org/10.1080/00268977000101561	journal	October 1970
The LaueUtil toolkit for Laue photocrystallography. I. Rapid orientation matrix determination for intermediate-size-unit-cell Laue data Kalinowski, Jarosław A.; Makal, Anna; Coppens, Philip Journal of Applied Crystallography, Vol. 44, Issue 6 https://doi.org/10.1107/S0021889811038143	journal	October 2011
The development of Laue techniques for single-pulse diffraction of chemical complexes: time-resolved Laue diffraction on a binuclear rhodium metal-organic complex Makal, Anna; Trzop, Elzbieta; Sokolow, Jesse Acta Crystallographica Section A Foundations of Crystallography, Vol. 67, Issue 4 https://doi.org/10.1107/S0108767311011883	journal	May 2011
Excited-state structure by time-resolved X-ray diffraction Kim, Christopher D.; Pillet, Sebastien; Wu, Guang Acta Crystallographica Section A Foundations of Crystallography, Vol. 58, Issue 2 https://doi.org/10.1107/S0108767301017986	journal	February 2002
An optical chopper for generation of short X-ray pulses to allow in-house time-resolved photocrystallography Kamiński, Radosław; Nottingham, Gary; Coppens, Philip Journal of Applied Crystallography, Vol. 47, Issue 5 https://doi.org/10.1107/S160057671401961X	journal	September 2014
CH/? hydrogen bonds in crystals Nishio, Motohiro CrystEngComm, Vol. 6, Issue 27 https://doi.org/10.1039/b313104a	journal	January 2004
On the refinement of time-resolved diffraction data: comparison of the random-distribution and cluster-formation models and analysis of the light-induced increase in the atomic displacement parameters Vorontsov, Ivan I.; Coppens, Philip Journal of Synchrotron Radiation, Vol. 12, Issue 4 https://doi.org/10.1107/S0909049505014561	journal	June 2005
Single-crystal-to-single-crystal E → Z isomerization of tiglic acid in a supramolecular framework Zheng, Shao-Liang; Messerschmidt, Marc; Coppens, Philip Acta Crystallographica Section B Structural Science, Vol. 63, Issue 4 https://doi.org/10.1107/S0108768107018538	journal	July 2007
A priori checking of the light-response and data quality before extended data collection in pump–probe photocrystallography experiments Coppens, Philip; Makal, Anna; Fournier, Bertrand Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 73, Issue 1 https://doi.org/10.1107/S2052520616017558	journal	January 2017
The LaueUtil toolkit for Laue photocrystallography. II. Spot finding and integration Kalinowski, Jarosław A.; Fournier, Bertrand; Makal, Anna Journal of Synchrotron Radiation, Vol. 19, Issue 4 https://doi.org/10.1107/S0909049512022637	journal	June 2012
Achieving Persistent Room Temperature Phosphorescence and Remarkable Mechanochromism from Pure Organic Luminogens Gong, Yongyang; Chen, Gan; Peng, Qian Advanced Materials, Vol. 27, Issue 40 https://doi.org/10.1002/adma.201502442	journal	September 2015
Enhancing Organic Phosphorescence by Manipulating Heavy-Atom Interaction Shi, Huifang; An, Zhongfu; Li, Pei-Zhou Crystal Growth & Design, Vol. 16, Issue 2 https://doi.org/10.1021/acs.cgd.5b01400	journal	January 2016
Shedding Light on the Photochemistry of Coinage-Metal Phosphorescent Materials: A Time-Resolved Laue Diffraction Study of an Ag ^I –Cu ^I Tetranuclear Complex Jarzembska, Katarzyna N.; Kamiński, Radosław; Fournier, Bertrand Inorganic Chemistry, Vol. 53, Issue 19 https://doi.org/10.1021/ic501696y	journal	September 2014
The nature of halogen.cntdot..cntdot..cntdot.halogen interactions: are short halogen contacts due to specific attractive forces or due to close packing of nonspherical atoms? Desiraju, Gautam R.; Parthasarathy, R. Journal of the American Chemical Society, Vol. 111, Issue 23 https://doi.org/10.1021/ja00205a027	journal	November 1989
CH/? hydrogen bonds in crystals Nishio, Motohiro CrystEngComm, Vol. 6, Issue 27 https://doi.org/10.1039/b313104a	journal	January 2004
Unexpected “amphoteric” character of the halogen bond: the charge density study of the co-crystal of N-methylpyrazine iodide with I2 Nelyubina, Yulia V.; Antipin, Mikhail Yu.; Dunin, Dmitriy S. Chemical Communications, Vol. 46, Issue 29 https://doi.org/10.1039/c0cc01094d	journal	January 2010
Efficient computer modeling of organic materials. The atom–atom, Coulomb–London–Pauli (AA-CLP) model for intermolecular electrostatic-polarization, dispersion and repulsion energies Gavezzotti, Angelo New Journal of Chemistry, Vol. 35, Issue 7 https://doi.org/10.1039/c0nj00982b	journal	January 2011
Assessment and validation of a screened Coulomb hybrid density functional Heyd, Jochen; Scuseria, Gustavo E. The Journal of Chemical Physics, Vol. 120, Issue 16 https://doi.org/10.1063/1.1668634	journal	April 2004
Efficient hybrid density functional calculations in solids: Assessment of the Heyd–Scuseria–Ernzerhof screened Coulomb hybrid functional Heyd, Jochen; Scuseria, Gustavo E. The Journal of Chemical Physics, Vol. 121, Issue 3, p. 1187-1192 https://doi.org/10.1063/1.1760074	journal	July 2004
Influence of the exchange screening parameter on the performance of screened hybrid functionals Krukau, Aliaksandr V.; Vydrov, Oleg A.; Izmaylov, Artur F. The Journal of Chemical Physics, Vol. 125, Issue 22 https://doi.org/10.1063/1.2404663	journal	December 2006
Can short-range hybrids describe long-range-dependent properties? Henderson, Thomas M.; Izmaylov, Artur F.; Scalmani, Giovanni The Journal of Chemical Physics, Vol. 131, Issue 4 https://doi.org/10.1063/1.3185673	journal	July 2009
Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg Hay, P. Jeffrey; Wadt, Willard R. The Journal of Chemical Physics, Vol. 82, Issue 1 https://doi.org/10.1063/1.448799	journal	January 1985
Extension of Gaussian‐2 theory to molecules containing third‐row atoms Ga–Kr Curtiss, Larry A.; McGrath, Mark P.; Blaudeau, Jean‐Philippe The Journal of Chemical Physics, Vol. 103, Issue 14 https://doi.org/10.1063/1.470438	journal	October 1995
Toward reliable density functional methods without adjustable parameters: The PBE0 model Adamo, Carlo; Barone, Vincenzo The Journal of Chemical Physics, Vol. 110, Issue 13 https://doi.org/10.1063/1.478522	journal	April 1999
The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors Boys, S.F.; Bernardi, F. Molecular Physics, Vol. 19, Issue 4, p. 553-566 https://doi.org/10.1080/00268977000101561	journal	October 1970
Data Reduction and Error Analysis for Accurate Single Crystal Diffraction Intensities Blessing, Robert H. Crystallography Reviews, Vol. 1, Issue 1 https://doi.org/10.1080/08893118708081678	journal	January 1987
Crystal Structure of 2,3,6,7-Tetrabromo-9,10-dihydro-9,10-ethanoanthracene Kitamura, Chitoshi; Hasegawa, Takayuki; Kawatsuki, Nobuhiro Analytical Sciences: X-ray Structure Analysis Online, Vol. 23 https://doi.org/10.2116/analscix.23.x207	journal	January 2007