The synthesis and structures of arene-substituted azadipyrromethenes

作者: Kullapa Chanawanno , Abed Hasheminasab , James T. Engle , Christopher J. Ziegler

DOI: 10.1016/J.POLY.2015.09.034

关键词:

摘要: Abstract We present the synthesis of several azadipyrromethenes with four peripheral arene units which can be readily generated via well-established chalcone synthetic method. The stability and yields these is highly dependent on nature substituent, bis-pyridine systems exhibiting highest degree instability. structures compounds their BF2 adducts are presented; intramolecular hydrogen bonding observed in free base ADPMs. also a study into absorption emission properties ADPMs observe that they identity substituents.

参考文章(23)
Aisling E. O'Connor, Margaret M. Mc Gee, Yury Likar, Vladimir Ponomarev, John J. Callanan, Donal F. O'shea, Annette T. Byrne, William M. Gallagher, Mechanism of cell death mediated by a BF2‐chelated tetraaryl‐azadipyrromethene photodynamic therapeutic: Dissection of the apoptotic pathway in vitro and in vivo International Journal of Cancer. ,vol. 130, pp. 705- 715 ,(2012) , 10.1002/IJC.26073
Lijuan Jiao, Yayang Wu, Sufan Wang, Xiaoke Hu, Ping Zhang, Changjiang Yu, Kebing Cong, Qianli Meng, Erhong Hao, M. Graça H. Vicente, Accessing Near-Infrared-Absorbing BF2-Azadipyrromethenes via a Push–Pull Effect Journal of Organic Chemistry. ,vol. 79, pp. 1830- 1835 ,(2014) , 10.1021/JO402160B
Aurore Loudet, Rakeshwar Bandichhor, Kevin Burgess, Aniello Palma, Shane O. McDonnell, Michael J. Hall, Donal F. O’Shea, B,O-chelated azadipyrromethenes as near-IR probes. Organic Letters. ,vol. 10, pp. 4771- 4774 ,(2008) , 10.1021/OL8018506
Thomas S. Teets, James B. Updegraff, Arthur J. Esswein, Thomas G. Gray, Three-Coordinate, Phosphine-Ligated Azadipyrromethene Complexes of Univalent Group 11 Metals Inorganic Chemistry. ,vol. 48, pp. 8134- 8144 ,(2009) , 10.1021/IC900208A
Saeed Attar, Zachary O’Brien, Hasan Alhaddad, Melissa L. Golden, Alejandro Calderón-Urrea, Ferrocenyl chalcones versus organic chalcones: a comparative study of their nematocidal activity. Bioorganic & Medicinal Chemistry. ,vol. 19, pp. 2055- 2073 ,(2011) , 10.1016/J.BMC.2011.01.048
Shane O. McDonnell, Donal F. O'Shea, Near-infrared sensing properties of dimethlyamino-substituted BF2-azadipyrromethenes. Organic Letters. ,vol. 8, pp. 3493- 3496 ,(2006) , 10.1021/OL061171X
André Bessette, Mihaela Cibian, Francis Bélanger, Denis Désilets, Garry S. Hanan, Introducing asymmetry in tetradentate azadipyrromethene chromophores: a systematic study of the impact on electronic and photophysical properties Physical Chemistry Chemical Physics. ,vol. 16, pp. 22207- 22221 ,(2014) , 10.1039/C4CP02629B
Nagappanpillai Adarsh, Madhesh Shanmugasundaram, Rekha R. Avirah, Danaboyina Ramaiah, Aza‐BODIPY Derivatives: Enhanced Quantum Yields of Triplet Excited States and the Generation of Singlet Oxygen and their Role as Facile Sustainable Photooxygenation Catalysts Chemistry: A European Journal. ,vol. 18, pp. 12655- 12662 ,(2012) , 10.1002/CHEM.201202438
Pierre-Antoine Bouit, Kenji Kamada, Patrick Feneyrou, Gérard Berginc, Loïc Toupet, Olivier Maury, Chantal Andraud, Two‐Photon Absorption‐Related Properties of Functionalized BODIPY Dyes in the Infrared Range up to Telecommunication Wavelengths Advanced Materials. ,vol. 21, pp. 1151- 1154 ,(2009) , 10.1002/ADMA.200801778
Xin-Dong Jiang, Yantao Fu, Tao Zhang, Weili Zhao, Synthesis and properties of NIR aza-BODIPYs with aryl and alkynyl substituents on the boron center Tetrahedron Letters. ,vol. 53, pp. 5703- 5706 ,(2012) , 10.1016/J.TETLET.2012.08.056