The synthesis and structures of arene-substituted azadipyrromethenes

被引:5
|
作者
Chanawanno, Kullapa [1 ]
Hasheminasab, Abed [1 ]
Engle, James T. [1 ]
Ziegler, Christopher J. [1 ]
机构
[1] Univ Akron, Dept Chem, Akron, OH 44325 USA
关键词
Azadipyrromethene; Boron difluoride; X-ray crystallography; UV-visible absorption; Fluorescence; BODIPY DYES; IN-VITRO; DERIVATIVES; COMPLEXES;
D O I
10.1016/j.poly.2015.09.034
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
We present the synthesis of several azadipyrromethenes with four peripheral arene units which can be readily generated via the well-established chalcone synthetic method. The stability and yields of these azadipyrromethenes is highly dependent on the nature of the arene substituent, with the bis-pyridine systems exhibiting the highest degree of instability. The structures of several of the compounds and their BF2 adducts are presented; intramolecular hydrogen bonding is observed in the free base ADPMs. We also present a study into the absorption and emission properties of the ADPMs and their BF2 adducts and observe that they are also highly dependent on the identity of the substituents. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:276 / 281
页数:6
相关论文
共 50 条
  • [1] SYNTHESIS, CHARACTERIZATION AND CRYSTAL-STRUCTURES OF A SERIES OF PENTANUCLEAR ARENE-SUBSTITUTED CLUSTERS
    LEWIS, J
    LI, CK
    DE ARELLANO, MCR
    RAITHBY, PR
    WONG, WT
    JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (09): : 1359 - 1363
  • [2] Practical Syntheses and Luminescent Properties of Arene-substituted Arsines
    Kihara, Hyota
    Imoto, Hiroaki
    Naka, Kensuke
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (10) : 2682 - 2689
  • [3] Synthesis and coordination chemistry of an arene-substituted tris(amido) redox-active ligand
    Munha, Rui F.
    Heyduk, Alan F.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [4] Synthesis and spectroscopic properties of arene-substituted pyrene derivatives as model compounds for fluorescent polarity probes
    Beinhoff, M
    Weigel, W
    Jurczok, M
    Rettig, W
    Modrakowski, C
    Brüdgam, I
    Hartl, H
    Schlüter, AD
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (20) : 3819 - 3829
  • [5] Parameterization of the Torsional Potential for Calix[4]arene-Substituted Poly(thiophene)s
    Preat, Julien
    Rodriguez-Ropero, Francisco
    Torras, Juan
    Bertran, Oscar
    Zanuy, David
    Aleman, Carlos
    JOURNAL OF COMPUTATIONAL CHEMISTRY, 2010, 31 (08) : 1741 - 1751
  • [6] Electron-donating arene-substituted pentacenedione derivatives: a study of structural, electronic, and electrochemical properties
    Younes, Eyad A.
    Hammad, Yamen J.
    Salami, Fatemeh
    Rasras, Anas J.
    Al-Qawasmeh, Raed A.
    Zhao, Yuming
    RSC ADVANCES, 2024, 14 (08) : 5331 - 5339
  • [7] An investigation into the tether length and substitution pattern of arene-substituted complexes for asymmetric transfer hydrogenation of ketones
    Cheung, Fung K.
    Lin, Changxue
    Minissi, Franco
    Criville, Adriana Lorente
    Graham, Mark A.
    Fox, David J.
    Wills, Martin
    ORGANIC LETTERS, 2007, 9 (22) : 4659 - 4662
  • [8] Molecular interaction studies in binary mixtures of tetrahydrofuran with arene-substituted alcohols: acoustic and volumetric study
    Shakila, A.
    Raju, R.
    Krishna, T. Srinivasa
    Dey, Ranjan
    Pandiyan, V
    PHYSICS AND CHEMISTRY OF LIQUIDS, 2020, 58 (02) : 263 - 279
  • [9] Synthesis of substituted arene molybdenum complexes by arene exchange
    Kündig, EP
    Fabritius, CH
    Grossheimann, G
    Romanens, P
    Butenschön, H
    Wey, HG
    ORGANOMETALLICS, 2004, 23 (15) : 3741 - 3744
  • [10] Application of β-Diketiminato Arene-Substituted Ru(II) Complexes in Highly Efficient H2 Dehydrocoupling of Amine Boranes
    Schreiber, Dominique F.
    O'Connor, Crystal
    Grave, Christian
    Ortin, Yannick
    Mueller-Bunz, Helge
    Phillips, Andrew D.
    ACS CATALYSIS, 2012, 2 (12): : 2505 - 2511