Synthesis and solid-state fluorescence properties of pentacyclic 7-substituted-indeno[1',2':4,5] pyrido [2,1-a] isoindol-5-ones

被引：6

作者：

Chamas, Z. ^{[1
]}

Marchi, E. ^{[2
]}

Presson, B. ^{[1
]}

Aubert, E. ^{[3
]}

Fort, Y. ^{[1
]}

Ceroni, P. ^{[2
]}

Mamane, V. ^{[1
]}

机构：

[1] Univ Lorraine, UMR CNRS 7565, Lab SRSMC, F-54506 Vandoeuvre Les Nancy, France

[2] Univ Bologna, Dept Chem G Ciamician, I-40126 Bologna, Italy

[3] Univ Lorraine, UMR CNRS 7036, Lab CRM2, F-54506 Vandoeuvre Les Nancy, France

来源：

RSC ADVANCES | 2015年 / 5卷 / 04期

基金：

欧洲研究理事会;

关键词：

PHOTOLUMINESCENCE; DERIVATIVES;

D O I：

10.1039/c4ra12155d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

With the aim to design fluorescent solids, a series of indeno[10,20: 4,5] pyrido[2,1-a] isoindol-5-ones with various substituents was prepared. In these pi-extended pentacyclic derivatives, the presence of a methyl group in the 7-position was found to have a critical influence on the fluorescence properties in the solid state. Crystal packing of the non-substituted derivatives shows strong p-p interactions causing quenching of the fluorescence. In contrast, by introducing a methyl substituent in the 7-position we obtained compounds with fluorescence quantum yield up to 32% in the solid state.

引用

页码：2715 / 2723

页数：9

共 50 条

[21] Molecular complexes of 4,10-dihydrothieno[3′,2′:5,6]pyrimido[2,1-a]isoindol-4-ones with β-cyclodextrin
Sergii Rudiuk
Zoia Voitenko
Sergii Riabov
Alexander Roshal
Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2007, 57 : 415 - 417
[22] Synthesis and reactions of 5-methylthieno[2′,3′:5,6]pyrimido[2,1-a]isoindol-4(5H)-one
Kysil, Andriy I.
Voitenko, Zoia V.
Wolf, Jean-Gerard
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2008, 73 (02) : 247 - 257
[23] Molecular complexes of 4,10-dihydrothieno[3′,2′:5,6]pyrimido[2,1-a]isoindol-4-ones with β-cyclodextrin
Rudiuk, Sergii
Voitenko, Zoia
Riabov, Sergii
Roshal, Alexander
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2007, 57 (1-4) : 415 - 417
[24] A Highly Selective Synthesis of (E)-11-Arylidenebenzo [4′,5′] thieno [2′,3′: 4,5] Pyrimido [2,1-a] Isoindol-13(1H)-ones via Copper-Catalyzed Sonogashira Coupling and Hydroamination
He, Heng
Wang, Zhen-Xu
Zhang, Mei-Mei
Liu, Jian-Quan
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (08)
[25] Synthesis of phenyl and substituted phenyl 3-ethyl-2,3,5,9b-tetrahydro[1,3]oxazolo[2,3-a]isoindol-5-ones
Nair, DS
Pauranik, V
Shah, AC
JOURNAL OF CHEMICAL RESEARCH, 2003, (12) : 772 - 774
[26] 1,2,3,9b-Tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones as a new class of respiratory syncytial virus (RSV) fusion inhibitors. Part 2: Identification of BTA9881 as a preclinical candidate
Bond, Silas
Draffan, Alistair G.
Fenner, Jennifer E.
Lambert, John
Lim, Chin Yu
Lin, Bo
Luttick, Angela
Mitchell, Jeffrey P.
Morton, Craig J.
Nearn, Roland H.
Sanford, Vanessa
Anderson, Kelly H.
Mayes, Penelope A.
Tucker, Simon P.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (04) : 976 - 981
[27] RETRACTED: Copper-Catalyzed Synthesis of Substituted Isoindolo[2,1-a]quinoxalines and Isoindolo[2,1-a]quinoxalin-6(5H)-ones (Retracted Article)
Biswas, Subhasish
Batra, Sanjay
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (22) : 4895 - 4902
[28] One-step synthesis, characterization and X-ray analysis of benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-ones
Lu, Lihua
He, Liang
JOURNAL OF MOLECULAR STRUCTURE, 2012, 1026 : 1 - 7
[29] Synthesis of 1H-pyrazolo [4′3′:5,6] pyrimido [2,1-A]-isoindol-4(10H)-ones.: Derivatives of a new ring system
Davoodnia, A
Bakavoli, M
Vahedinia, A
Rahimizadeh, M
Roshani, M
HETEROCYCLES, 2006, 68 (04) : 801 - 806
[30] Pyrido[2′,3′:4,5]pyrrolo[2,1-d][1,2,3,5]tetrazine-4(3H)-ones, a new class of temozolomide heteroanalogues
Diana, Patrizia
Stagno, Antonina
Barraja, Paola
Montalbano, Alessandra
Martorana, Annamaria
Carbone, Anna
Dattolo, Gaetano
Cirrincione, Girolamo
ARKIVOC, 2009, : 177 - 186

← 1 2 3 4 5 →