SYNTHESIS OF NOVEL BISPHENOL-BIPHENANTHROLINE-BASED MOLECULAR TWEEZERS

Öz

A molecular “dugdugi” 8 derived from 1,10-phenanthroline  was synthesized and characterized by using NMR, EIMS and UV studies. Bisphenol was alkylated with 1,3-dibromopropane and reacted with 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol to obtain 8. 30 mmolL^-1 solution of 8 was prepared in 10 % DMF in ethanol and was stirred for 30 min with 30 m L^-1 ethanolic solutions of Co²⁺, Cr³⁺, Cu²⁺, Fe³⁺, Mn²⁺, Ni²⁺, Ag⁺, and Zn²⁺. Chemosensor 8 switched-on in the presence of Fe³⁺ by showing pink color while it remained turn-off in the presence of other metals. The UV spectra of the molecular “dugdugi” showed a peak at 279 nm which shifted to 290 nm after interacting with Fe³⁺. A new peak also appeared at 524 nm.

Anahtar Kelimeler

• Fe3+ chemosensor, imidazole, naked-eye chemosensors, molecular switch

MOLEKÜLER CIMBIZLAMAYA DAYALI YENİ BİR BISFENOL-BIPHENANTHROLINE SENTEZİ

Öz

1,10-fenantrolin’den elde edilen "dugdugi" 8 molekülü sentezlendi ve NMR, EIMS ve UV kullanılarak yapısı aydınlatıldı. Bisfenol 8’I elde etmek için 1,3dibrompropan kullanılarak alkillendi ve 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol ile reaksiyona sokuldu. Molekül 8’in 30 molL-1 çözeltisi %10 DMF içeren etanolde hazırlandı, ve etanol ile hazırlanmış 30 m L-1 Co2+, Cr3+, Cu2+, Fe3+, Mn2+, Ni2+, Ag+, and Zn2+ çözeltisi ile 30 dakika karıştırıldı.Kemosensör 8, Fe3+ varlığında pembe renk vererek çalışırken, diğer metallerin varlığında ayırt edici bir renk gözlenmedi. "Dugdugi" nin moleküler UV spektrumunda 279 nm’de bulunan pik Fe3+ ile etkileştirilince 290 nm’ye kaydı. Ayrıca, 524 nm’de yeni bir pik oluştuğu görüldü

Anahtar Kelimeler

• Fe3+ Kemosensör, İmidazol, Çıplak Gözle Kemosensör, Moleküler Anahtar

Kaynakça

1. Raymo FM, Giordani S. All-optical processing with molecular switches. P Natl Acad Sci USA, 2002, 99(8): 4941-4944
2. Akkaya EU. Squaraine-based long wavelength fluorescent chemosensors for ions - the design, synthesis and characterization of a new class of red to nir fluorescent chemosensors. Nato Adv Sci I C-Mat, 1997, 492(177-188
3. Kim HN, Ren WX, Kim JS, et al. Fluorescent and colorimetric sensors for detection of lead, cadmium, and mercury ions. Chemical Society Reviews, 2012, 41(8): 3210-3244
4. Zhao Q, Li F, Huang C. Phosphorescent chemosensors based on heavy-metal complexes. Chemical Society Reviews, 2010, 39(8): 3007-3030
5. Abalos T, Moragues M, Royo S, et al. Dyes that bear thiazolylazo groups as chromogenic chemosensors for metal cations. Eur J Inorg Chem, 2012, 1): 76-84
6. Abebe FA, Sinn E. Fluorescein-based fluorescent and colorimetric chemosensors for copper in aqueous media. Tetrahedron Lett, 2011, 52(41): 5234-5237
7. Zhang PS, Chen J, Huang FH, et al. One-pot fabrication of polymer nanoparticle-based chemosensors for cu2+ detection in aqueous media. Polym Chem-Uk, 2013, 4(7): 2325-2332
8. Santos-Figueroa LE, Moragues ME, Climent E, et al. Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the years 2010-2011. Chemical Society Reviews, 2013, 42(8): 3489-3613

9. Sharma S, Hundal MS, Hundal G. Dual channel chromo/fluorogenic chemosensors for cyanide and fluoride ions - an example of in situ acid catalysis of the strecker reaction for cyanide ion chemodosimetry. Org Biomol Chem, 2013, 11(4): 654-661
10. Martínez-Máñez R, Sancenón F. Fluorogenic and chromogenic chemosensors and reagents for anions. Chemical Reviews, 2003, 103(11): 4419-4476
11. Huang XH, He YB, Hu CG, et al. Synthesis and chiral recognition properties of novel fluorescent chemosensors for amino acid. J Fluoresc, 2009, 19(1): 97-104
12. Zhang HX, Hua XF, Tuo XL, et al. Polystyrene microsphere-based lanthanide luminescent chemosensor for detection of organophosphate pesticides. J Rare Earth, 2012, 30(12): 1203-1207
13. Obare SO, De C, Guo W, et al. Fluorescent chemosensors for toxic organophosphorus pesticides: A review. Sensors-Basel, 2010, 10(7): 7018-7043
14. Ojida A, Hamachi I. Design and synthesis of bis(zn(ii)-dipicolylamine)-based fluorescent artificial chemosensors for phosphorylated proteins/peptides. B Chem Soc Jpn, 2006, 79(1): 35-46
15. Xie YZ, Shan GG, Zhou ZY, et al. Schiff-base as highly sensitive and reversible chemosensors for hcl gas. Sensor Actuat B-Chem, 2013, 177:41-49
16. Krcmar D, Prica M, Dalmacija B, et al. Correlation of different pollution criteria in the assessment of metal sediment pollution. J Environ Sci Heal A, 2013, 48(4): 380-393
17. Swamy KMK, Kim MJ, Jeon HR, et al. New 7-hydroxycoumarin-based fluorescent chemosensors for zn(ii) and cd(ii). B Korean Chem Soc, 2010, 31(12): 3611-3616
18. Caltagirone C, Bencini A, Demartin F, et al. Redox chemosensors: Coordination chemistry towards cu-ii, zn-ii, cd-ii, hg-ii, and pb-ii of 1-aza-4,10-dithia-7-oxacyclododecane ([12]anens(2)o) and its n-ferrocenylmethyl derivative. Dalton T, 2003, 5): 901-909
19. Meng XM, Zhu MZ, Liu L, et al. Novel highly selective fluorescent chemosensors for zn(ii). Tetrahedron Lett, 2006, 47(10): 1559-1562
20. Liu L, Zhang GX, Xiang JF, et al. Fluorescence "turn on" chemosensors for ag+ and hg2+ based on tetraphenylethylene motif featuring adenine and thymine moieties. Org Lett, 2008, 10(20): 4581-4584
21. Fu Y, Mu L, Zeng X, et al. An nbd-armed thiacalix[4]arene-derived colorimetric and fluorometric chemosensor for ag+: A metal-ligand receptor of anions. Dalton T, 2013, 42(10): 3552-3560
22. Nuriman, Kuswandi B, Verboom W. Selective chemosensor based on 7-nitrobenzofurazan in tripodal structure for the detection of hg(ii) ions in environmental and cosmetic samples. Sensor Lett, 2011, 9(4): 1316-1322
23. Zor E, Saf AO, Bingol H. Spectrophotometric and voltammetric characterization of a novel selective electroactive chemosensor for mg2+. Cent Eur J Chem, 2013, 11(4): 554-560
24. Zhou YM, Zhang JL, Zhang L, et al. A rhodamine-based fluorescent enhancement chemosensor for the detection of cr3+ in aqueous media. Dyes Pigments, 2013, 97(1): 148-154
25. Zhang DW, Dong ZY, Jiang XZ, et al. A proof-of-concept fluorescent strategy for highly selective detection of cr(vi) based on inner filter effect using a hydrophilic ionic chemosensor. Anal Methods-Uk, 2013, 5(7): 1669-1675
26. Xu HR, Li K, Liu Q, et al. Dianthracene-cyclen conjugate: The first equal-equivalent responding fluorescent chemosensor for pb2+ in aqueous solution. Analyst, 2013, 138(8): 2329-2334
27. Maity SB, Bharadwaj PK. A chemosensor built with rhodamine derivatives appended to an aromatic platform via 1,2,3-triazoles: Dual detection of aluminum(iii) and fluoride/acetate ions. Inorg Chem, 2013, 52(3): 1161-1163
28. Yong X, Su MJ, Wang W, et al. A naked-eye chemosensor for fluoride ions: A selective easy-to-prepare test paper. Org Biomol Chem, 2013, 11(14): 2254-2257
29. Li SW, Cao XF, Chen CS, et al. Novel salicylic acid-oriented thiourea-type receptors as colorimetric chemosensor: Synthesis, characterizations and selective naked-eye recognition properties. Spectrochim Acta A, 2012, 96(18-23
30. Ceylan A, Bas SZ, Bayrakci M, et al. Synthesis and spectroscopic studies of novel rhodanine azo dyes: An excellent selective chemosensor for naked-eye detecting of cu2+ ion. Acta Chim Slov, 2012, 59(3): 656-663
31. Suresh P, Azath IA, Pitchumani K. Naked-eye detection of fe3+ and ru3+ in water: Colorimetric and ratiometric sensor based on per-6-amino-beta-cyclodextrin/p-nitrophenol. Sensor Actuat B-Chem, 2010, 146(1): 273-277
32. Balraj C, Elango KP. Spectroscopic studies on the intermolecular charge transfer interaction of fe(ii)- and fe(iii)-phthalocyanines with 2,3,5,6-tetrachloro-1,4-benzoquinone and its application in colorimetric sensing of amino acids and amines. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2012, 86(0): 44-50
33. Wu S-P, Chen Y-P, Sung Y-M. Colorimetric detection of fe3+ ions using pyrophosphate functionalized gold nanoparticles. Analyst, 2011, 136(9): 1887-1891
34. Xiang Y, Tong AJ. A new rhodamine-based chemosensor exhibiting selective fe-iii-amplified fluorescence. Org Lett, 2006, 8(8): 1549-1552
35. Feng L, Chen Z, Wang D. Selective sensing of fe3+ based on fluorescence quenching by 2,6-bis(benzoxazolyl)pyridine with β-cyclodextrin in neutral aqueous solution. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2007, 66(3): 599-603
36. Liu J-M, Zheng Q-Y, Yang J-L, et al. A new fluorescent chemosensor for fe3+ and cu2+ based on calix[4]arene. Tetrahedron Lett, 2002, 43(50): 9209-9212
37. Jung HJ, Singh N, Lee DY, et al. Benzimidazole-based ratiometric fluorescent receptor exhibiting molecular logic gate for cu2+ and fe3+. Tetrahedron Lett, 2009, 50(40): 5555-5558
38. Mitra A, Ramanujam B, Rao CP. 1-(d-glucopyranosyl-2′-deoxy-2′-iminomethyl)-2-hydroxynaphthalene as chemo-sensor for fe3+ in aqueous hepes buffer based on colour changes observable with the naked eye. Tetrahedron Lett, 2009, 50(7): 776-780
39. Avirah RR, Jyothish K, Ramaiah D. Dual-mode semisquaraine-based sensor for selective detection of hg2+ in a micellar medium. Org Lett, 2007, 9(1): 121-124
40. Xiang Y, Li M, Chen XT, et al. Highly sensitive and selective optical chemosensor for determination of cu2+ in aqueous solution. Talanta, 2008, 74(5): 1148-1153
41. Wei D, Sun Y, Yin J, et al. Design and application of fe3+ probe for “naked-eye” colorimetric detection in fully aqueous system. Sensors and Actuators B: Chemical, 2011, 160(1): 1316-1321
42. Zhan J, Wen L, Miao F, et al. Synthesis of a pyridyl-appended calix[4]arene and its application to the modification of silver nanoparticles as an fe3+ colorimetric sensor. New Journal of Chemistry, 2012, 36(3): 656-661
43. Li Z, Zhang L, Li X, et al. A fluorescent color/intensity changed chemosensor for fe3+ by photo-induced electron transfer (pet) inhibition of fluoranthene derivative. Dyes Pigments, 2012, 94(1): 60-65
44. Beér R. The encyclopedia of tibetan symbols and motifs. Place Published: Serindia,2004: 258
45. Herrero C, Hughes JL, Quaranta A, et al. Intramolecular light induced activation of a salen-mn-iii complex by a ruthenium photosensitizer. Chem Commun, 2010, 46(40): 7605-7607