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    Aroyleneimidazophenazine: A Sensitive Probe for Detecting CN− Anion and its Solvatochromism Effect (English)

    In: Journal of heterocyclic chemistry ; 52 , 6 ; 1699-1704 ; 2015
    • ISSN:
      0022-152X
    • Article (Journal)  /  Print

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    A novel electron‐deficient heteroacene 15 H ‐pyrazino[2″,3″:3′,4′]pyrrolo[1′,2′:1,2]imidazo[4,5‐ b ]phenazin‐15‐one ( 1 ) has been successfully synthesized and characterized. Compound 1 can selectively recognize CN − and F − over other 10 anions including BF 4 − , PF 6 − , Cl − , SO 4 2− , NO 3 − , I − , H 2 PO 4 − , ClO 4 − , Ac − , and Br − in CHCl 3 /DMF mixed solvents with dual responses, including absorption signals and fluorescent “turn‐off” effects. CN − and F − can be distinguished by the completely quenched fluorescence (for CN − ) and partially reduced fluorescence (for F − ). Especially, compound 1 exhibits higher sensitivity to CN − than F − with the response concentration as low as 5.0 × 10 −6  mol/L. Moreover, compound 1 shows very interesting solvatochromism effect, and the CHCl 3 solution of compound 1 is sensitive to triethylamine, and its emission could change from green to red upon the addition of triethylamine, which is attributed to the n–π intermolecular charge‐transfer interaction.

    Table of contents – Volume 52, Issue 6

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    1595
    1,2,4‐Triazine Chemistry Part IV: Synthesis and Chemical Behavior of 3‐Functionalized 5,6‐Diphenyl‐1,2,4‐triazines towards Some Nucleophilic and Electrophilic Reagents
    Abdel‐Rahman, Reda M. / Makki, Mohamed S. T. / Ali, Tarik E. / Ibrahim, Magdy A. et al. | 2015
    1608
    An Improved, Scalable and Impurity‐Free Process for Lixivaptan
    Mu, Shuai / Niu, Duan / Liu, Ying / Zhang, Dashuai / Liu, Dengke / Liu, Changxiao et al. | 2015
    1614
    Synthesis of 6‐(5‐Methylisoxazol‐3yl)‐3‐alkyl Sulfanyl‐[1,2,4]triazolo‐[3,4‐b][1,3,4]thiadiazoles
    Vaarla, Krishnaiah / Vedula, Rajeswar Rao et al. | 2015
    1618
    Synthesis of 2,5‐Disubstituted Derivatives of Pyrano[2,3‐d][1,3]thiazines via the Interaction of 2‐Substituted 4‐Hydroxy‐6H‐1,3‐thiazine‐6‐ones with Aldehydes
    Shutov, Roman V. / Sopova, Marina V. / Krylov, Alexander V. / Kaluzhskikh, Andry N. / Ivin, Boris А. et al. | 2015
    1625
    An Efficient Synthesis of Chromeno[4,3‐d]isoxazolo[5,4‐b]pyridin‐6‐one Derivatives
    Jin, Pei‐Pei / Liu, Xue‐Cheng / Liu, De‐Qi / Huang, Zhi‐Bin / Shi, Da‐Qing et al. | 2015
    1631
    Fused Quinazolinoquinazolinones: Synthesis, Isomerization, Spectroscopic Identification, and Anticancer Activity []
    Venkateswarlu, Somepalli / Satyanarayana, Meka / Lakshmikanthan, Vijaybaskar / Siddaiah, Vidavalur et al. | 2015
    1639
    Efficient Microwave‐assisted One‐pot Synthesis of Novel Spironaphthopyrano‐one Derivatives
    Meshram, G. / Wagh, P. / Amratlal, V. / Deshpande, S. et al. | 2015
    1646
    Diastereoselective Synthesis of Novel Pyrrolidine or Pyrrolizine‐Fused Benzo‐δ‐sultams via 1,3‐Dipolar Cycloadditions
    Ghandi, Mehdi / Kia, Maryam Asle / Sadeghzadegh, Masoud / Bozcheloei, Abolfazl Hasani / Kubicki, Maciej et al. | 2015
    1654
    Design, Synthesis, and Antioxidant/Antidiabetic Activity of Nucleic Acid Bases Bearing Fused N,S‐Heterocyclic Phosphor Esters
    Abdou, Wafaa M. / Kamel, Azza A. / Khidre, Maha D. et al. | 2015
    1663
    Convenient and Efficient Synthesis of 11‐Amino‐2,8‐substituted‐2,3,8,9‐tetrahydrobenzo[4,5]thieno[2,3‐b]quinolinone Derivatives
    Wang, Zhong‐Xia / Chen, Li‐Zhuang / Li, Bei / Han, Guang‐Fan et al. | 2015
    1669
    Sequence Selective Michael Addition for Synthesis of Indeno‐Pyridine and Indeno‐Pyran Derivatives in One‐Pot Reaction Using CuO Nanoparticles in Water
    Valekar, Navanath J. / Patil, Prasad P. / Gore, Anil H. / Kolekar, Govind B. / Deshmukh, Madhukar B. / Anbhule, Prashant V. et al. | 2015
    1677
    Facile Synthesis of Novel Selenium‐Containing Benzopyrans
    Zsótér, Zsolt / Tímár, Tibor / Kónya, Krisztina / Patonay, Tamás / Jekő, József et al. | 2015
    1684
    Synthesis of Some Novel 3‐Substituted Indole Derivatives Using Polyamine Functionalized Heterogeneous Catalyst
    Magar, Rupali L. / Thorat, Prashant B. / Waware, Jagdish L. / More, Rameshwar R. / Solanke, Usha A. / Patil, Bhagwan R. / Pawar, Rajendra P. et al. | 2015
    1693
    Synthesis of Novel Dibenzylbutyrolactones as Dimethylmatairesinol Analogues
    Heidary Alizadeh, Babak / Foroumadi, Alireza / Kobarfard, Farzad / Saeedi, Mina / Shafiee, Abbas et al. | 2015
    1699
    Aroyleneimidazophenazine: A Sensitive Probe for Detecting CN− Anion and its Solvatochromism Effect
    Zhao, J. / Li, J. / Li, G. / Gao, J. / Kjelleberg, S. L. A. / Loo, S. C. J. / Zhang, Q. et al. | 2015
    1705
    1,3‐Benzothiazoles as Antimicrobial Agents
    Defrenza, Ivana / Catalano, Alessia / Carocci, Alessia / Carrieri, Antonio / Muraglia, Marilena / Rosato, Antonio / Corbo, Filomena / Franchini, Carlo et al. | 2015
    1713
    Synthesis, Characterization, and Antibacterial Activity of Some Novel Substituted Imidazole Derivatives via One‐pot Three‐Component
    Ramagiri, Raj Kumar / Thupurani, Murali Krishna / Vedula, Rajeswar Rao et al. | 2015
    1718
    Exploiting the 1,2,3‐Triazole Moiety to Generate Carbazole Molecular Architectures through Click Approach
    Ameen, Mohamed A. / El‐Shaieb, Kamal M. / Mohamed, Asmaa H. / Abdel‐Latif, Fathy F. et al. | 2015
    1723
    Novel Tandem Aldol Intramolecular Cyclization of Substituted N‐Benzylpiperidine‐4‐one: Synthesis of Novel‐Type Nitrogen 2,8‐Phenanthroline Heterocycles
    Kostochka, Michael L. / Zajicek, Jaroslav / Fuselier, Joseph A. / Etienne, Marcus A. / Sun, Lichun / Coy, David H. et al. | 2015
    1731
    Design and Synthesis of Novel 2‐(1,2,4‐triazol‐1‐yl)‐quinoline‐Based Tricyclic 1,5‐benzothiazepine Derivatives
    Huang, Le / Fei, Ting‐Hong / Hu, Kun / Liu, Fang‐Ming et al. | 2015
    1737
    Microwave‐assisted Synthesis of 6‐{(5‐Aryl‐1,3,4‐oxadiazol‐2‐yl)methyl}‐6H‐indolo[2,3‐b]quinoxalines
    Avula, Sreenivas / Komsani, Jayaram Reddy / Koppireddi, Satish / Yadla, Rambabu et al. | 2015
    1743
    Synthesis and In Vitro Cytotoxic Activity of Novel Triazole‐Isoxazole Derivatives
    Najafi, Zahra / Mahdavi, Mohammad / Safavi, Maliheh / Saeedi, Mina / Alinezhad, Heshmatollah / Pordeli, Mahboobeh / Kabudanian Ardestani, Sussan / Shafiee, Abbas / Foroumadi, Alireza / Akbarzadeh, Tahmineh et al. | 2015
    1748
    A Highly Efficient Catalyst for the Suzuki Cross‐coupling Reaction of 3‐Chloro‐5‐oxadiazol‐2‐yl Pyridine
    Sajith, A. M. / Abdul Khader, K. K. / Muralidharan, A. / Ali Padusha, M. S. / Nagaswarupa, H. P. et al. | 2015
    1758
    Synthesis of Potentially Antioxidant and Antibacterial Biologically Active Thiazolidines
    Aly [1], Ashraf A. / Ishak [2], Esam A. / El Malah, Tamer / Brown, Alan B. / Elayat, Wael M. et al. | 2015
    1765
    Synthesis of New Spirocyclopropane and Oxadiazole Products
    Haouas, Amel / Hamadi[1], Naoufel Ben / Msaddek, Moncef et al. | 2015
    1769
    Synthesis, Crystal Structure, and Antibacterial Activity of 1,2,4‐Triazoles and 1,2,4‐Triazol‐3‐one
    Ben Salah, Bochra / Chaari, Najla / Rekik, Awatef / Ben Hsouna, Anis / Trigui, Mohamed / Kossentini, Mohamed et al. | 2015
    1776
    Synthesis of 1‐Arylethyl‐2‐arylethylamino‐5‐trifluoroacetyl‐1,2,3,4‐tetrahydropyridines and Related Compounds with Potential Cell Efflux Pump Inhibition
    Zanatta, Nilo / Lobo, Marcio M. / dos Santos, Josiane M. / Souza, Laura de A. / de Andrade, Valquiria P. / Bonacorso, Helio G. / Martins, Marcos A. P. et al. | 2015
    1782
    Synthesis, Characterization, Novel Interaction of DNA, Antioxidant and Antimicrobial Studies of New Water Soluble Metallophthalocyanines Posture Eight Hydroxyphenyl Moiety via 1,3,4‐oxadiazole Bridge
    Basappa, Chidananda / Reddy, Venugopala K. R. / Kotresh, Harish M. N. / Musturappa, Pradeep K. / Devendrachari, Mruthyunjayachari C. / Ganesh, Shimoga D. et al. | 2015
    1792
    Regioselective Synthesis of Some New Pyrazolo[1,5‐a]pyrimidines, Pyrazolo[1,5‐a]quinazoline and Pyrimido[4′,5′:3,4]pyrazolo[1,5‐a] pyrimidines Containing Thiazole Moiety
    Bondock, Samir / Tarhoni, Abd El‐Gaber / Fadda, Ahmed A. et al. | 2015
    1800
    Convenient One‐Pot Room Temperature Synthesis of 2‐(trifluoromethyl)‐1,2,3,4,7,8‐hexahydroquinolin‐5(6H)‐one derivatives via Catalyst‐Free Multicomponent Reactions
    Liang‐Ce, Rong / Tao, Shimin / Zha, Yunyun / Xia, Sheng / Gao, Yanian / Chen, Ming et al. | 2015
    1806
    One‐pot Synthesis of Highly Functionalized Tetrahydropyridines: A Camphoresulfonic Acid Catalyzed Multicomponent Reaction
    Bharti, Ruchi / Parvin, Tasneem et al. | 2015
    1812
    Product and Mechanism of Gas‐phase Pyrolysis of 2‐arylidinehydrazinopyrimidines: Interesting Route to Condensed Heterocycles[1]
    Al‐Awadi, Sundus A. / Ibrahim, Maher R. / El‐Dusouqui, Osman M. E. / Al‐Awadi, Nouria A. et al. | 2015
    1817
    A Facile Synthesis of Some New 1‐Benzothiazolyl‐3‐aryl/Hetaryl‐5‐(3‐aryl‐1‐phenyl‐4‐pyrazolyl) Pyrazoles and Their Antimicrobial Activity
    Singh, Sushma / Punia, Vijaykiran / Sharma, Chetan / Aneja, K. R. / Prakash, Om / Pundeer, Rashmi et al. | 2015
    1823
    Copper(0) Nanoparticles in Click Chemistry: Synthesis of 3,5‐Disubstituted Isoxazoles
    Vishwanatha, T. M. / Sureshbabu, Vommina V. et al. | 2015
    1834
    Benzimidazole Annulated New Heterocyclic Compounds: Synthesis of Polycyclic Pyrrole Derivatives
    Raslan, Mohamed A. / Khalil, Mohamed A. / Sayed, Samia M. et al. | 2015
    1839
    A Facile and Efficient Approach to Seven‐membered Heterocycles by Chlorosilane‐catalyzed Domino Reaction
    Wang, Min / Wang, Lingtian / Guo, Qin / Ge, Junjun / Lin, Deqing / Ye, Xiaoxia et al. | 2015
    1844
    New One Pot‐synthesis of Functionally Substituted Pyridines from Enaminoketones
    El‐Taweel, Fathy / Abou Elmaaty, Tarek et al. | 2015
    1848
    Catalyst‐Free and Green Synthesis of Some Novel Benzamide Derivatives
    Samani Ghaleh Taki, Banafshe / Rostami, Mahbubeh / Mirkhani, Valiollah / Moghadam, Majid / Mohammadpoor‐Baltork, Iraj / Tangestaninejad, Shahram / Jamali Moghadam, Ahmad / Kia, Reza et al. | 2015
    1858
    Unexpected Formation of Thioglycolurils Precursors
    Gazieva, Galina A. / Kravchenko, Angelina N. et al. | 2015
    1864
    The Design and Synthesis of Novel 2,3‐Dihydrobenzo[f]isoquinolin‐4(1H)‐ones via Sequential Ugi–Heck Reactions by Using an Efficient Heterogeneous Palladium Nanocatalyst
    Rasouli, Mohammad Ali / Miri, Simin / Rashidi Ranjbar, Parviz et al. | 2015
    1871
    KAl(SO4)2.12H2O(Alum): An Efficient Catalyst for the Synthesis of Novel bis[spiro(quinazoline‐oxindole)] Derivatives Via One‐Pot Pseudo Five‐Component Reactions
    Mohammadi, Ali A. / Taheri, Salman / Askari, Saber / Ahdenov, Reza et al. | 2015
    1876
    An Elegant Synthesis of a New Class of 1‐(Substituted)‐1H‐1,2,3‐triazol‐4‐yl)methyl)diphenylphosphineoxides by Microwave Irradiation
    Chinthaparthi, Radha Rani / Gangireddy, Chandra Sekhar Reddy / Kandula, Madhu Kumar Reddy / Balam, Satheesh Krishna / Cirandur, Suresh Reddy et al. | 2015
    1883
    An Efficient Synthesis of 3‐(3‐benzyl‐2‐(phenylimino)‐2,3‐dihydrothiazol‐4‐yl)‐6‐methyl‐4‐(2‐oxo‐2‐phenylethoxy)‐3,4‐dihydro‐2H‐pyran‐2‐one Derivatives via Multi‐Component Approach
    Bade, Thirupaiah / Vedula, Rajeswar Rao et al. | 2015
    1887
    Synthesis and Herbicidal Evaluation of 4,6‐Dimethoxyaurone Derivatives
    Zhang, Min / Chen, Guo‐Yan / Li, Ting / Liu, Bin / Deng, Jie‐Yu / Zhang, Li / Yang, Liu‐Qing / Xu, Xiao‐Hua et al. | 2015
    1893
    A New and Efficient One‐Pot Synthesis of 2‐Fluoroalkyl Substituted Indoles
    Wang, Zengxue / Ma, Qingwen et al. | 2015
    1897
    One‐pot Multicomponent Synthesis of Isoxazolyl Spiro[indoline‐3,2′‐pyrrolidine]‐2,4′‐diones Catalyzed by CAN
    Rajanarendar, Eligeti / Kishore, Baireddy / Ramakrishna, Saini et al. | 2015
    1902
    Enantiospecific Synthesis of (–)‐Cuspareine and (–)‐Galipinine
    Chacko, Shibin / Ramapanicker, Ramesh et al. | 2015
    1907
    Green Biginelli‐type Reaction: Solvent‐free Synthesis of 5‐unsubstituted 3,4‐dihydropyrimdin‐2(1H)‐ones
    Wang, Min / Song, Jilei / Lu, Qilin / Wang, Qinglin et al. | 2015
    1911
    An Efficient Synthesis of 4‐Arylmethylidene‐3‐substituted‐Isoxazol‐5(4H)‐ones in Aqueous Medium
    Chavan, Abhijit P. / Pinjari, Avinash B. / Mhaske, Pravin C. et al. | 2015
    1916
    Erratum
    | 2015

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