Benzimidazole derivatives: Selective fluorescent chemosensors for the picogram detection of picric acid

Journal of Organic Chemistry

Volumn 79, Issue 23, 2014, Pages 11619-11630

  Xiong, Jin Feng ^a   Li, Jian Xiao ^c   Mo, Guang Zhen ^a   Huo, Jing Pei ^c   Liu, Jin Yan ^a   Chen, Xiao Yun ^d   Wang, Zhao Yang ^a,b  

^a SOUTH CHINA NORMAL UNIVERSITY   (China)

^b BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

^c SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^d RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; FLUORESCENCE; PHYSIOLOGY;

BENZENE DERIVATIVES; BENZIMIDAZOLE DERIVATIVES; CONTACT MODES; FLUORESCENT CHEMOSENSOR; FLUORESCENT CHEMOSENSORS; HIGH SENSITIVITY; NITROAROMATIC EXPLOSIVES; PICOGRAM LEVEL;

EXPLOSIVES DETECTION;

1,3,5 TRI(1H BENZO[D]IMIDAZOL 2 YL)BENZENE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; PICRIC ACID; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; ELECTRON; ENERGY TRANSFER; FLUORESCENCE; FLUORESCENCE ANALYSIS; FLUORESCENT CHEMOSENSOR; LIMIT OF DETECTION; MOLECULAR SENSOR; PHOTOCHEMICAL QUENCHING; QUANTUM YIELD; STEREOSPECIFICITY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET RADIATION;

EID: 84916241130     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502281b     Document Type: Article

References (57)

1. Bhattacharjee, Y. Science 2008, 320, 1416-1417
2. Germain, M. E.; Knapp, M. J. Chem. Soc. Rev. 2009, 38, 2543-2555
3. Zhang, K.; Zhou, H.; Mei, Q.; Wang, S.; Guan, G.; Liu, R.; Zhang, J.; Zhang, Z. J. Am. Chem. Soc. 2011, 133, 8424-8427
4. Liao, Y. Z.; Strong, V.; Wang, Y.; Li, X. G.; Wang, X.; Kaner, R. B. Adv. Funct. Mater. 2012, 22, 726-735
5. Nagarkar, S. S.; Joarder, B.; Chaudhari, A. K.; Mukherjee, S.; Ghosh, S. K. Angew. Chem., Int. Ed. 2013, 52, 2881-2885
6. Bejoymohandas, K. S.; George, T. M.; Bhattacharya, S.; Natarajan, S.; Reddy, M. L. P. J. Mater. Chem. C 2014, 2, 515-523
7. Tian, D.; Li, Y.; Chen, R. Y.; Chang, Z.; Wang, G. Y.; Bu, X. H. J. Mater. Chem. A 2014, 2, 1465-1470
8. Liu, T. H.; Ding, L. P.; He, G.; Yang, Y.; Wang, W. L.; Fang, Y. ACS Appl. Mater. Interfaces 2011, 3, 1245-1253
9. Ma, Y. X.; Li, H.; Peng, S.; Wang, L. Y. Anal. Chem. 2012, 84, 8415-8421
10. Bhalla, V.; Kaur, S.; Vij, V.; Kumar, M. Inorg. Chem. 2013, 52, 4860-4865
11. Li, X. G.; Liao, Y. Z.; Huang, M. R.; Strong, V.; Kaner, R. B. Chem. Sci. 2013, 4, 1970-1978
12. Xu, Y. Q.; Li, B. H.; Li, W. W.; Zhao, J.; Sun, S. G.; Pang, Y. Chem. Commun. 2013, 49, 4764-4766
13. Kumar, S.; Venkatramaiah, N.; Patil, S. J. Phys. Chem. C 2013, 117, 7236-7245
14. Venkatramaiah, N.; Kumar, S.; Patil, S. Chem. Commun. 2012, 48, 5007-5009
15. Kumar, M.; Reja, S. I.; Bhalla, V. Org. Lett. 2012, 14, 6084-6087
16. Samanta, D.; Mukherjee, P. S. Dalton Trans. 2013, 42, 16784-16795
17. Zhou, X. H.; Li, L.; Li, H. H.; Li, A.; Yang, T.; Huang, W. Dalton Trans. 2013, 42, 12403-12409
18. Li, H. M.; Zhu, Y. X.; Zhang, J. Y.; Chi, Z. G.; Chen, L. P.; Su, C. Y. RSC Adv. 2013, 3, 16340-16344
19. Bhalla, V.; Gupta, A.; Kumar, M.; Rao, D. S.; Prasad, S. K. ACS Appl. Mater. Interfaces 2013, 5, 672-679
20. Vij, V.; Bhalla, V.; Kumar, M. ACS Appl. Mater. Interfaces 2013, 5, 5373-5380
21. Dey, N.; Samanta, S. K.; Bhattacharya, S. ACS Appl. Mater. Interfaces 2013, 5, 8394-8400
22. Bhalla, V.; Gupta, A.; Kumar, M. Org. Lett. 2012, 14, 3112-3115
23. Bhalla, V.; Arora, H.; Singh, H.; Kumar, M. Dalton Trans. 2013, 42, 969-974
24. Roy, B.; Bar, A. K.; Gole, B.; Mukherjee, P. S. J. Org. Chem. 2013, 78, 1306-1310
25. Valeur, B. Molecular fluorescence: Principle and applications; Wiley-VCH: Weinheim, 2002.
26. Mao, Z. Z.; Wang, Z. Y.; Li, J. N.; Song, X. M.; Luo, Y. F. Synth. Commun. 2010, 40, 1963-1977
27. Frei, R.; Breitbach, A. S.; Blackwell, H. E. Angew. Chem., Int. Ed. 2012, 51, 5226-5229
28. Narasimhan, B.; Sharma, D.; Kumar, P. Med. Chem. Res. 2012, 21, 269-283
29. Peng, P.; Xiong, J. F.; Mo, G. Z.; Zheng, J. L.; Chen, R. H.; Chen, X. Y.; Wang, Z. Y. Amino Acids 2014, 46, 2427-2433
30. Wiggins, K. M.; Kerr, R. L.; Chen, Z.; Bielawski, C. W. J. Mater. Chem. 2010, 20, 5709-5714
31. Muth, M.; Rasco-Orozco, M.; Thelakkat, M. Adv. Funct. Mater. 2011, 21, 4510-4518
32. Xiong, J. F.; Luo, S. H.; Huo, J. P.; Liu, J. Y.; Chen, S. X.; Wang, Z. Y. J. Org. Chem. 2014, 79, 8366-8373
33. Xiong, J. F.; Luo, S. H.; Wang, Q. F.; Wang, Z. Y.; Qi, J. Des. Monomers Polym. 2013, 16, 389-397
34. Zhu, K.; Vukotic, V. N.; Loeb, S. J. Angew. Chem., Int. Ed. 2012, 51, 2168-2172
35. He, Q. T.; Li, X. P.; Liu, Y.; Yu, Z. Q.; Wang, W.; Su, C. Y. Angew. Chem., Int. Ed. 2009, 48, 6156-6159
36. Guo, Z.; Song, N. R.; Moon, J. H.; Kim, M.; Jun, E. J.; Choi, J.; Lee, J. Y.; Bielawski, C. W.; Sessler, J. L.; Yoon, J. J. Am. Chem. Soc. 2012, 134, 17846-17849
37. Tan, Y. H.; Li, J. X.; Xue, F. L.; Qi, J.; Wang, Z. Y. Tetrahedron 2012, 68, 2827-2843
38. Huo, J. P.; Luo, J. C.; Wu, W.; Xiong, J. F.; Mo, G. Z.; Wang, Z. Y. Ind. Eng. Chem. Res. 2013, 52, 11850-11857
39. Chen, R. H.; Xiong, J. F.; Peng, P.; Mo, G. Z.; Tang, X. S.; Wang, Z. Y.; Wang, X. F. Asian J. Chem. 2014, 26, 926-932
40. Bhalla, V.; Singh, H.; Kumar, M.; Prasad, S. K. Langmuir 2011, 27, 15275-15281
41. Wang, B.; Liu, C. J.; Wang, J. D.; Lei, Z. K.; Hu, D. L. Chem. J. Chin. Univ. 2012, 33, 76-81
42. Tanabe, K.; Suzui, Y.; Hasegawa, M.; Kato, T. J. Am. Chem. Soc. 2012, 134, 5652-5661
43. Ahipa, T. N.; Kumar, V.; Adhikari, A. V. Liq. Cryst. 2013, 40, 31-38
44. Vieira, A. A.; Gallardo, H.; Barberá, J.; Romero, P.; Serrano, J. L.; Sierra, T. J. Mater. Chem. 2011, 21, 5916-5922
45. Shanmugaraju, S.; Joshi, S. A.; Mukherjee, P. S. J. Mater. Chem. 2011, 21, 9130-9138
46. Ueki, T.; Watanabe, M. Macromolecules 2008, 41, 3739-3749
47. Iwan, A.; Kaczmarczyk, B.; Jarzabek, B.; Jurusik, J.; Domanski, M.; Michalak, M. J. Phys. Chem. A 2008, 112, 7556-7566
48. Zuo, Z. C.; Fu, Y. Z.; Manthiram, A. Polymers 2012, 4, 1627-1644
49. Fu, Y. Z.; Manthiram, A. J. Electrochem. Soc. 2007, 154, B8-B12
50. Pramanik, S.; Bhalla, V.; Kumar, M. Anal. Chim. Acta 2013, 793, 99-106
51. Wang, J.; Mei, J.; Yuan, W. Z.; Liu, P.; Qin, A. J.; Sun, J. Z.; Ma, Y. G.; Tang, B. Z. J. Mater. Chem. 2011, 21, 4056-4059
52. Li, D. D.; Liu, J. Z.; Kwok, R. T.; Liang, Z. Q.; Tang, B. Z.; Yu, J. H. Chem. Commun. 2012, 48, 7167-7169
53. Venkatramaiah, N.; Kumar, S.; Patil, S. Chem.-Eur. J. 2012, 18, 14745-14751
54. Martinez, H. P.; Grant, C. D.; Reynolds, J. G.; Trogler, W. C. J. Mater. Chem. 2012, 22, 2908-2914
55. Kartha, K. K.; Babu, S. S.; Srinivasan, S.; Ajayaghosh, A. J. Am. Chem. Soc. 2012, 134, 4834-4841
56. Bhalla, V.; Pramanik, S.; Kumar, M. Chem. Commun. 2013, 49, 895-897
57. Kumar, M.; Vij, V.; Bhalla, V. Langmuir 2012, 28, 12417-12421