Structurally Diverse Pyrene-decorated Planar Chiral [2,2]Paracyclophanes with Tunable Circularly Polarized Luminescence between Monomer and Excimer
© 2023 Wiley-VCH GmbH..
We reported the synthesis of a series of structurally diverse CPL-active molecules, in which pyrene units were installed to chiral pm/po-[2,2]PCP scaffolds either with or without a triple bond spacer for pm/po-PCP-P1 and pm/po-PCP-P2, respectively. The X-ray crystallographic analyses revealed that these pyrene-based [2,2]PCP derivatives exhibited diverse structures and crystal packings in the solid phases. The pyrene-based [2,2]PCP derivatives exhibit various (chir)optical properties in organic solutions, depending on their respective structures. In a mixture of dioxane and water, pm/po-PCP-P1 emit green excimer fluorescence, whereas pm/po-PCP-P2 emit blue one. The chiroptical investigation demonstrated that Rp-pm-PCP-P1 and Rp-pm-PCP-P2 exhibited completely opposite CD and CPL signals even they possess the same chiral Rp-[2,2]PCP core. The same argument also holds for other chiral pyrene-based [2,2]PCP derivatives. The theoretical calculation revealed that these unusual phenomena were attributed to different orientation between transition electric dipole moments and the magnetic dipole moments originating from the presence or absence of a triple bond spacer. These pyrene-based [2,2]PCP derivatives display various colours and fluorescence emissions in the solid state and PMMA films, possibly due to the different packings as observed in the crystal structure. Moreover, these compounds also can interact with perylene diimide through π-π interactions, leading to near-white fluorescence.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:30 |
|---|---|
| Enthalten in: |
Chemistry (Weinheim an der Bergstrasse, Germany) - 30(2024), 12 vom: 26. Feb., Seite e202303819 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Lian, Zhe [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
Circularly polarized luminescence |
|---|
| Anmerkungen: |
Date Revised 27.02.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
|---|
| doi: |
10.1002/chem.202303819 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM364887699 |
|---|
| LEADER | 01000caa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM364887699 | ||
| 003 | DE-627 | ||
| 005 | 20240229163805.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231226s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/chem.202303819 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1308.xml |
| 035 | |a (DE-627)NLM364887699 | ||
| 035 | |a (NLM)37997515 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Lian, Zhe |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Structurally Diverse Pyrene-decorated Planar Chiral [2,2]Paracyclophanes with Tunable Circularly Polarized Luminescence between Monomer and Excimer |
| 264 | 1 | |c 2024 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Revised 27.02.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2023 Wiley-VCH GmbH. | ||
| 520 | |a We reported the synthesis of a series of structurally diverse CPL-active molecules, in which pyrene units were installed to chiral pm/po-[2,2]PCP scaffolds either with or without a triple bond spacer for pm/po-PCP-P1 and pm/po-PCP-P2, respectively. The X-ray crystallographic analyses revealed that these pyrene-based [2,2]PCP derivatives exhibited diverse structures and crystal packings in the solid phases. The pyrene-based [2,2]PCP derivatives exhibit various (chir)optical properties in organic solutions, depending on their respective structures. In a mixture of dioxane and water, pm/po-PCP-P1 emit green excimer fluorescence, whereas pm/po-PCP-P2 emit blue one. The chiroptical investigation demonstrated that Rp-pm-PCP-P1 and Rp-pm-PCP-P2 exhibited completely opposite CD and CPL signals even they possess the same chiral Rp-[2,2]PCP core. The same argument also holds for other chiral pyrene-based [2,2]PCP derivatives. The theoretical calculation revealed that these unusual phenomena were attributed to different orientation between transition electric dipole moments and the magnetic dipole moments originating from the presence or absence of a triple bond spacer. These pyrene-based [2,2]PCP derivatives display various colours and fluorescence emissions in the solid state and PMMA films, possibly due to the different packings as observed in the crystal structure. Moreover, these compounds also can interact with perylene diimide through π-π interactions, leading to near-white fluorescence | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Circularly polarized luminescence | |
| 650 | 4 | |a Excimer | |
| 650 | 4 | |a High quantum yield | |
| 650 | 4 | |a Paracyclophanes | |
| 650 | 4 | |a Pyrene | |
| 700 | 1 | |a Liu, Lin |e verfasserin |4 aut | |
| 700 | 1 | |a He, Jing |e verfasserin |4 aut | |
| 700 | 1 | |a Fan, Shimin |e verfasserin |4 aut | |
| 700 | 1 | |a Guo, Shengzhu |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Xiaonan |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Guoqin |e verfasserin |4 aut | |
| 700 | 1 | |a Fan, Yanqing |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Xuebo |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Meng |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Chuanfeng |e verfasserin |4 aut | |
| 700 | 1 | |a Jiang, Hua |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Chemistry (Weinheim an der Bergstrasse, Germany) |d 1996 |g 30(2024), 12 vom: 26. Feb., Seite e202303819 |w (DE-627)NLM09455398X |x 1521-3765 |7 nnns |
| 773 | 1 | 8 | |g volume:30 |g year:2024 |g number:12 |g day:26 |g month:02 |g pages:e202303819 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1002/chem.202303819 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 30 |j 2024 |e 12 |b 26 |c 02 |h e202303819 | ||