How does the interplay between bromine substitution at bay area and bulky substituents at imide position influence the photophysical properties of perylene diimides?
This article reports a comparative study on the synthesis, self-assembly, and photophysical properties of perylene diimides (PDIs) symmetrically tethered with long alkyl chains or polyhedral oligomeric silsesquioxanes (POSS) at the imide position and/or bromo substitutions at 1,7-positions of the ba...
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| Published in | RSC advances Vol. 7; no. 26; pp. 16155 - 16162 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Cambridge
Royal Society of Chemistry
01.01.2017
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| Subjects | |
| Online Access | Get full text |
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| Abstract | This article reports a comparative study on the synthesis, self-assembly, and photophysical properties of perylene diimides (PDIs) symmetrically tethered with long alkyl chains or polyhedral oligomeric silsesquioxanes (POSS) at the imide position and/or bromo substitutions at 1,7-positions of the bay area. This series of samples include dodecyl-PDI
H
-dodecyl (
1
), dodecyl-PDI
Br
-dodecyl (
2
), POSS-PDI
H
-POSS (
3
), and POSS-PDI
Br
-POSS (
4
). In solution, the PDIs with bromine substitution at bay area (
2
,
4
) exhibit red-shifted absorption maximum compared to those without (
1
,
3
), which is consistent with a twisted perylene chromophore as revealed by molecular simulation. Similar bathochromatic shift was observed on the solid crystal state emission of
2
as compared to
1
. However, in crystals, the emission spectrum of
4
exhibits a seemingly hypochromatic shift relative to that of
3
, which could be rationalized by their packing in the crystals. The bromo substitution is believed to partially quench the fluorescence and the relatively loose packing of the twisted π-plane of
4
may not be able to confine π-plane in place, leaving multiple pathways for fluorescent quenching rather than red-shifted emission. While both
3
and
4
exhibit a unique dimer packing scheme, the dimers have quite different longitudinal offset and transverse offset of the π-plane. The longitudinal offset in dimers of
4
is so large that the naphthalene moieties in the dimer almost adopt a face-to-face arrangement and their mutual interactions are considered relatively independent. All these contribute to the less red-shifted fluorescent emission and the lower fluorescent yields in crystals of
4
relative to
3
as compared to that in solution. The study shall shed light into the complicated mutual interactions among intrinsic electronic structure, microscopic molecular packing, and the macroscopic optoelectronic properties.
This article reports a comparative study on the photophysical properties of perylene diimides which caused by the interplay between bromine substitution at bay area and bulky substituents at imide position. |
|---|---|
| AbstractList | This article reports a comparative study on the synthesis, self-assembly, and photophysical properties of perylene diimides (PDIs) symmetrically tethered with long alkyl chains or polyhedral oligomeric silsesquioxanes (POSS) at the imide position and/or bromo substitutions at 1,7-positions of the bay area. This series of samples include dodecyl–PDIH–dodecyl (1), dodecyl–PDIBᵣ–dodecyl (2), POSS–PDIH–POSS (3), and POSS–PDIBᵣ–POSS (4). In solution, the PDIs with bromine substitution at bay area (2, 4) exhibit red-shifted absorption maximum compared to those without (1, 3), which is consistent with a twisted perylene chromophore as revealed by molecular simulation. Similar bathochromatic shift was observed on the solid crystal state emission of 2 as compared to 1. However, in crystals, the emission spectrum of 4 exhibits a seemingly hypochromatic shift relative to that of 3, which could be rationalized by their packing in the crystals. The bromo substitution is believed to partially quench the fluorescence and the relatively loose packing of the twisted π-plane of 4 may not be able to confine π-plane in place, leaving multiple pathways for fluorescent quenching rather than red-shifted emission. While both 3 and 4 exhibit a unique dimer packing scheme, the dimers have quite different longitudinal offset and transverse offset of the π-plane. The longitudinal offset in dimers of 4 is so large that the naphthalene moieties in the dimer almost adopt a face-to-face arrangement and their mutual interactions are considered relatively independent. All these contribute to the less red-shifted fluorescent emission and the lower fluorescent yields in crystals of 4 relative to 3 as compared to that in solution. The study shall shed light into the complicated mutual interactions among intrinsic electronic structure, microscopic molecular packing, and the macroscopic optoelectronic properties. This article reports a comparative study on the synthesis, self-assembly, and photophysical properties of perylene diimides (PDIs) symmetrically tethered with long alkyl chains or polyhedral oligomeric silsesquioxanes (POSS) at the imide position and/or bromo substitutions at 1,7-positions of the bay area. This series of samples include dodecyl–PDIH–dodecyl (1), dodecyl–PDIBr–dodecyl (2), POSS–PDIH–POSS (3), and POSS–PDIBr–POSS (4). In solution, the PDIs with bromine substitution at bay area (2, 4) exhibit red-shifted absorption maximum compared to those without (1, 3), which is consistent with a twisted perylene chromophore as revealed by molecular simulation. Similar bathochromatic shift was observed on the solid crystal state emission of 2 as compared to 1. However, in crystals, the emission spectrum of 4 exhibits a seemingly hypochromatic shift relative to that of 3, which could be rationalized by their packing in the crystals. The bromo substitution is believed to partially quench the fluorescence and the relatively loose packing of the twisted π-plane of 4 may not be able to confine π-plane in place, leaving multiple pathways for fluorescent quenching rather than red-shifted emission. While both 3 and 4 exhibit a unique dimer packing scheme, the dimers have quite different longitudinal offset and transverse offset of the π-plane. The longitudinal offset in dimers of 4 is so large that the naphthalene moieties in the dimer almost adopt a face-to-face arrangement and their mutual interactions are considered relatively independent. All these contribute to the less red-shifted fluorescent emission and the lower fluorescent yields in crystals of 4 relative to 3 as compared to that in solution. The study shall shed light into the complicated mutual interactions among intrinsic electronic structure, microscopic molecular packing, and the macroscopic optoelectronic properties. This article reports a comparative study on the synthesis, self-assembly, and photophysical properties of perylene diimides (PDIs) symmetrically tethered with long alkyl chains or polyhedral oligomeric silsesquioxanes (POSS) at the imide position and/or bromo substitutions at 1,7-positions of the bay area. This series of samples include dodecyl-PDI H -dodecyl ( 1 ), dodecyl-PDI Br -dodecyl ( 2 ), POSS-PDI H -POSS ( 3 ), and POSS-PDI Br -POSS ( 4 ). In solution, the PDIs with bromine substitution at bay area ( 2 , 4 ) exhibit red-shifted absorption maximum compared to those without ( 1 , 3 ), which is consistent with a twisted perylene chromophore as revealed by molecular simulation. Similar bathochromatic shift was observed on the solid crystal state emission of 2 as compared to 1 . However, in crystals, the emission spectrum of 4 exhibits a seemingly hypochromatic shift relative to that of 3 , which could be rationalized by their packing in the crystals. The bromo substitution is believed to partially quench the fluorescence and the relatively loose packing of the twisted π-plane of 4 may not be able to confine π-plane in place, leaving multiple pathways for fluorescent quenching rather than red-shifted emission. While both 3 and 4 exhibit a unique dimer packing scheme, the dimers have quite different longitudinal offset and transverse offset of the π-plane. The longitudinal offset in dimers of 4 is so large that the naphthalene moieties in the dimer almost adopt a face-to-face arrangement and their mutual interactions are considered relatively independent. All these contribute to the less red-shifted fluorescent emission and the lower fluorescent yields in crystals of 4 relative to 3 as compared to that in solution. The study shall shed light into the complicated mutual interactions among intrinsic electronic structure, microscopic molecular packing, and the macroscopic optoelectronic properties. This article reports a comparative study on the photophysical properties of perylene diimides which caused by the interplay between bromine substitution at bay area and bulky substituents at imide position. This article reports a comparative study on the synthesis, self-assembly, and photophysical properties of perylene diimides (PDIs) symmetrically tethered with long alkyl chains or polyhedral oligomeric silsesquioxanes (POSS) at the imide position and/or bromo substitutions at 1,7-positions of the bay area. This series of samples include dodecyl–PDI H –dodecyl ( 1 ), dodecyl–PDI Br –dodecyl ( 2 ), POSS–PDI H –POSS ( 3 ), and POSS–PDI Br –POSS ( 4 ). In solution, the PDIs with bromine substitution at bay area ( 2 , 4 ) exhibit red-shifted absorption maximum compared to those without ( 1 , 3 ), which is consistent with a twisted perylene chromophore as revealed by molecular simulation. Similar bathochromatic shift was observed on the solid crystal state emission of 2 as compared to 1 . However, in crystals, the emission spectrum of 4 exhibits a seemingly hypochromatic shift relative to that of 3 , which could be rationalized by their packing in the crystals. The bromo substitution is believed to partially quench the fluorescence and the relatively loose packing of the twisted π-plane of 4 may not be able to confine π-plane in place, leaving multiple pathways for fluorescent quenching rather than red-shifted emission. While both 3 and 4 exhibit a unique dimer packing scheme, the dimers have quite different longitudinal offset and transverse offset of the π-plane. The longitudinal offset in dimers of 4 is so large that the naphthalene moieties in the dimer almost adopt a face-to-face arrangement and their mutual interactions are considered relatively independent. All these contribute to the less red-shifted fluorescent emission and the lower fluorescent yields in crystals of 4 relative to 3 as compared to that in solution. The study shall shed light into the complicated mutual interactions among intrinsic electronic structure, microscopic molecular packing, and the macroscopic optoelectronic properties. |
| Author | Zhang, Wen-Bin Shao, Yu Lin, Yuejian Yang, Shuguang Zhu, Meifang Sun, Bin Wang, Jing Zhang, Xinlin Liang, Kai |
| AuthorAffiliation | Department of Chemistry Center for Soft Matter Science and Engineering Fudan University Peking University Key Laboratory of Polymer Chemistry & Physics of Ministry of Education Donghua University Center for Advanced Low-dimension Materials South China University of Science and Technology College of Chemistry and Molecular Engineering College of Materials Science and Engineering State Key Laboratory for Modification of Chemical Fibers and Polymer Materials South China Advanced Institute of Soft Matter Science and Technology |
| AuthorAffiliation_xml | – sequence: 0 name: Center for Soft Matter Science and Engineering – sequence: 0 name: State Key Laboratory for Modification of Chemical Fibers and Polymer Materials – sequence: 0 name: Department of Chemistry – sequence: 0 name: Key Laboratory of Polymer Chemistry & Physics of Ministry of Education – sequence: 0 name: Peking University – sequence: 0 name: South China University of Science and Technology – sequence: 0 name: Fudan University – sequence: 0 name: College of Materials Science and Engineering – sequence: 0 name: South China Advanced Institute of Soft Matter Science and Technology – sequence: 0 name: Center for Advanced Low-dimension Materials – sequence: 0 name: Donghua University – sequence: 0 name: College of Chemistry and Molecular Engineering |
| Author_xml | – sequence: 1 givenname: Yu surname: Shao fullname: Shao, Yu – sequence: 2 givenname: Xinlin surname: Zhang fullname: Zhang, Xinlin – sequence: 3 givenname: Kai surname: Liang fullname: Liang, Kai – sequence: 4 givenname: Jing surname: Wang fullname: Wang, Jing – sequence: 5 givenname: Yuejian surname: Lin fullname: Lin, Yuejian – sequence: 6 givenname: Shuguang surname: Yang fullname: Yang, Shuguang – sequence: 7 givenname: Wen-Bin surname: Zhang fullname: Zhang, Wen-Bin – sequence: 8 givenname: Meifang surname: Zhu fullname: Zhu, Meifang – sequence: 9 givenname: Bin surname: Sun fullname: Sun, Bin |
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| CitedBy_id | crossref_primary_10_1007_s11307_023_01800_1 crossref_primary_10_1002_anie_202310445 crossref_primary_10_1002_chem_201800895 crossref_primary_10_1039_C7RA04296E crossref_primary_10_3390_molecules24112114 crossref_primary_10_1002_chem_201806337 crossref_primary_10_1002_ange_202310445 crossref_primary_10_1002_slct_201800267 crossref_primary_10_1016_j_jssc_2021_122665 crossref_primary_10_3390_molecules25225324 crossref_primary_10_1039_D0CY01982H crossref_primary_10_1016_j_poly_2023_116638 crossref_primary_10_3390_nano14211733 crossref_primary_10_1021_jacs_0c10457 crossref_primary_10_1039_C7SM01918A crossref_primary_10_1002_cphc_201900716 crossref_primary_10_1117_1_JBO_29_8_085001 |
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| Notes | 2 10.1039/c7ra00779e 4 Electronic supplementary information (ESI) available: Experimental section, detailed characterization of and the X-ray crystallographic data for the structure of and energy-minimized molecular models of CCDC 1527259. For ESI and crystallographic data in CIF or other electronic format see DOI ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
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| Snippet | This article reports a comparative study on the synthesis, self-assembly, and photophysical properties of perylene diimides (PDIs) symmetrically tethered with... |
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| SubjectTerms | Bromine Chromophores Comparative studies Computer simulation Crystallography Crystals Dimers Electronic structure Emission Fluorescence moieties molecular dynamics Molecular structure Naphthalene Optoelectronics Polyhedral oligomeric silsesquioxane Properties (attributes) Self-assembly silsesquioxanes Substitutes |
| Title | How does the interplay between bromine substitution at bay area and bulky substituents at imide position influence the photophysical properties of perylene diimides? |
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