Theoretical study on molecular packing and electronic structure of bi-1,3,4-oxadiazole derivatives

Handle URI:
http://hdl.handle.net/10754/563251
Title:
Theoretical study on molecular packing and electronic structure of bi-1,3,4-oxadiazole derivatives
Authors:
Wang, Haitao; Bai, Fuquan; Jia, Xiaoshi; Cao, Di; Ravva, Mahesh Kumar ( 0000-0001-9619-0176 ) ; Bredas, Jean-Luc ( 0000-0001-7278-4471 ) ; Qu, Songnan; Bai, Binglian; Zhang, Hongxing; Li, Min
Abstract:
The molecular aggregation structure of 5,5′-bis(naphthalen-2-yl)-2,2′-bi(1,3,4-oxadiazole) (BOXD-NP) was studied by computing the intermolecular interaction potential energy surface (PES) at density functional theory level based on a dimer model. All B3LYP, CAM-B3LYP and M062x functionals can yield a reliable isolated molecular geometry. The conformation of BOXD-NP obtained with all methods is perfectly planar, indicating good conjugation ability between oxadiazole and naphthalene rings. The vibrational frequencies of BOXD-NP were also calculated using the B3LYP/6-311+G∗∗ method, which showed great consistency with the experimental observations and makes the assignments of the IR spectra more solid. It was revealed that the lowest excited state of BOXD-NP should be assigned as a highly allowed π-π∗ state by TD-DFT calculation. Considering the non-covalent interactions in molecular aggregates, the M062x functional was applied in the construction of the PES. Besides the packing structure found in the crystals, PES also predicted several stable structures, indicating that PES has great ability in guiding molecular self-assembly. Symmetry Adapted Perturbation Theory (SAPT) analysis on these energy-minimum molecular stacking structures revealed that London dispersion forces are the strongest attractive component in the binding. This journal is
KAUST Department:
Physical Sciences and Engineering (PSE) Division; Materials Science and Engineering Program; Solar and Photovoltaic Engineering Research Center (SPERC)
Publisher:
Royal Society of Chemistry (RSC)
Journal:
RSC Adv.
Issue Date:
2014
DOI:
10.1039/c4ra06405d
Type:
Article
ISSN:
20462069
Sponsors:
Author H.W. would like to thank Dr Jian Wang (Jilin University) for providing HPC skills. This work was supported by National Science Foundation of China (51103057, 51073071, 21173096, 21072076, and 21003057), and Postdoctoral Science Foundation of China (2012T50294).
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Materials Science and Engineering Program; Solar and Photovoltaic Engineering Research Center (SPERC)

Full metadata record

DC FieldValue Language
dc.contributor.authorWang, Haitaoen
dc.contributor.authorBai, Fuquanen
dc.contributor.authorJia, Xiaoshien
dc.contributor.authorCao, Dien
dc.contributor.authorRavva, Mahesh Kumaren
dc.contributor.authorBredas, Jean-Lucen
dc.contributor.authorQu, Songnanen
dc.contributor.authorBai, Binglianen
dc.contributor.authorZhang, Hongxingen
dc.contributor.authorLi, Minen
dc.date.accessioned2015-08-03T11:44:07Zen
dc.date.available2015-08-03T11:44:07Zen
dc.date.issued2014en
dc.identifier.issn20462069en
dc.identifier.doi10.1039/c4ra06405den
dc.identifier.urihttp://hdl.handle.net/10754/563251en
dc.description.abstractThe molecular aggregation structure of 5,5′-bis(naphthalen-2-yl)-2,2′-bi(1,3,4-oxadiazole) (BOXD-NP) was studied by computing the intermolecular interaction potential energy surface (PES) at density functional theory level based on a dimer model. All B3LYP, CAM-B3LYP and M062x functionals can yield a reliable isolated molecular geometry. The conformation of BOXD-NP obtained with all methods is perfectly planar, indicating good conjugation ability between oxadiazole and naphthalene rings. The vibrational frequencies of BOXD-NP were also calculated using the B3LYP/6-311+G∗∗ method, which showed great consistency with the experimental observations and makes the assignments of the IR spectra more solid. It was revealed that the lowest excited state of BOXD-NP should be assigned as a highly allowed π-π∗ state by TD-DFT calculation. Considering the non-covalent interactions in molecular aggregates, the M062x functional was applied in the construction of the PES. Besides the packing structure found in the crystals, PES also predicted several stable structures, indicating that PES has great ability in guiding molecular self-assembly. Symmetry Adapted Perturbation Theory (SAPT) analysis on these energy-minimum molecular stacking structures revealed that London dispersion forces are the strongest attractive component in the binding. This journal isen
dc.description.sponsorshipAuthor H.W. would like to thank Dr Jian Wang (Jilin University) for providing HPC skills. This work was supported by National Science Foundation of China (51103057, 51073071, 21173096, 21072076, and 21003057), and Postdoctoral Science Foundation of China (2012T50294).en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleTheoretical study on molecular packing and electronic structure of bi-1,3,4-oxadiazole derivativesen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentMaterials Science and Engineering Programen
dc.contributor.departmentSolar and Photovoltaic Engineering Research Center (SPERC)en
dc.identifier.journalRSC Adv.en
dc.contributor.institutionKey Laboratory of Automobile Materials (MOE), College of Materials Science and Engineering, Jilin UniversityChangchun, Chinaen
dc.contributor.institutionKey Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin UniversityChangchun, Chinaen
dc.contributor.institutionKey Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of SciencesChangchun, Chinaen
dc.contributor.institutionCollege of Physics, Jilin UniversityChangchun, Chinaen
kaust.authorBredas, Jean-Lucen
kaust.authorRavva, Mahesh Kumaren
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