Synthesis of 7,12-bis(4-(di(1H-pyrrol-2-yl)methyl)phenyl)benzo[k]fluoranthene from a new dialdehyde as a novel fluorometric bis-Dipyrromethane derivative

Synthesis of 7,12-bis(4-(di(1H-pyrrol-2-yl)methyl)phenyl)benzo[k]fluoranthene from a new dialdehyde as a novel fluorometric bis-Dipyrromethane derivative

Dipyrromethanes are useful mediator structures which can be used as a part of other molecules such as bis-porphyrins and their derivations. Various methods have been developed for their synthesis. This study presents the synthesis of a new bisdipyrromethane, 7,12-bis(4-(di(1H-pyrrol-2-yl)methyl)phenyl)benzo[k]fluoranthene, using the Lewis acid catalyzed reaction between a new dialdehyde and pyrrole at room temperature. The UV spectroscopic and fluorometric properties of the final product and precursors were determined. The newly synthesized product with desirable UV spectroscopic and fluorometric properties has the potential to be applied as a part of bisporphyrins or it can be used for other purposes in future studies.

___

  • 1. Gryko DT, Gryko D, Lee, Chang-H. 5-Substituted dipyrranes: synthesis and reactivity. Chemical Society Reviews 2012; 41 (10): 3780- 3789.
  • 2. Lee, Chang-H, Lindsey JS. One-flask synthesis of meso-substituted dipyrromethanes and their application in the synthesis of transsubstituted porphyrin building blocks. Tetrahedron 1994; 50 (39): 11427-11440.
  • 3. Zaidi SHH, Fico RM, Lindsey JS. Investigation of streamlined syntheses of porphyrins bearing distinct meso substituents. Organic Process Research & Development 2006; 10 (1): 118-134.
  • 4. Gryko DT, Clausen C, Lindsey J S, Thiol-derivatized porphyrins for attachment to electroactive surfaces. The Journal of Organic Chemistry 1999; 64 (23): 8635-8647.
  • 5. Awuah SG, You Y. Boron dipyrromethene (BODIPY)-based photosensitizers for photodynamic therapy. Rsc Advances 2012; 2 (30): 11169-11183.
  • 6. Galangau O, Dumas-Verdes C, Méallet-Renault R, Clavier G. Rational design of visible and NIR distyryl-BODIPY dyes from a novel fluorinated platform. Organic & biomolecular chemistry 2010: 8 (20): 4546-4553.
  • 7. Josefsen LB, Boyle RW. Unique diagnostic and therapeutic roles of porphyrins and phthalocyanines in photodynamic therapy, imaging and theranostics. Theranostics 2012; 2 (9): 916.
  • 8. Kursunlu AN, Guler E, Ucan HI, Boyle RW. A novel Bodipy-Dipyrrin fluorescent probe: Synthesis and recognition behaviour towards Fe (II) and Zn (II). Dyes and Pigments 2012; 94 (3): 496-502.
  • 9. Ulrich G, Ziessel R, Harriman A. Die vielseitige Chemie von Bodipy‐Fluoreszenzfarbstoffen. Angewandte Chemie 2008; 120 (7): 1202- 1219 (in German).
  • 10. Boens N, Leen V, Dehaen W. Erratum: Fluorescent indicators based on BODIPY (Chemical Society Reviews (2012) 41 (1130-1172). Chemical Society Reviews 2012; 41 (24): 8212.
  • 11. Ulrich G, Ziessel R, Harriman A. The chemistry of fluorescent bodipy dyes: versatility unsurpassed. Angewandte Chemie International Edition 2008; 47 (7): 1184-1201.
  • 12. Lindsey JS. Synthetic routes to meso-patterned porphyrins. Accounts of Chemical Research 2009; 43 (2): 300-311. 13. Beyzavi MH, Lentz D, Reissig HU, Wiehe A. Synthesis of functionalized, sterically congested calix [4] phyrin macrocycles using donor– acceptor‐substituted cyclopropanes–first example of a mono‐meso‐spirolactone incorporated into a calix [4] phyrin. European Journal of Organic Chemistry 2013; 2013 (2): 269-282.
  • 14. Dudicˇ M, Lhota P, Lang K, Stibor I. Synthesis of novel porphyrin-based biscalix [4] arenes. Tetrahedron letters 1999; 40 (32): 5949-5952.
  • 15. Laha JK, Dhanalekshmi S, Taniguchi M, Ambroise A, Lindsey JS. A scalable synthesis of meso-substituted dipyrromethanes. Organic Process Research & Development 2003; 7 (6): 799-812.
  • 16. Sreedevi KG, Thomas AP, Salini P, Ramakrishnan S, Anju K et al. 5, 5-Diaryldipyrromethanes: syntheses and anion binding properties. Tetrahedron Letters 2011; 52 (45): 5995-5999.
  • 17. Tsuchimoto T, Hatanaka K, Shirakawa E, Kawakami Y. Indium triflate-catalysed double addition of heterocyclic arenes to alkynes. Chemical Communications 2003; (19): 2454-2455.
  • 18. Sessler JL, Hugdahl J, Johnson MR. A convenient synthesis of a “gable”-type porphyrin. The Journal of Organic Chemistry 1986; 51 (14): 2838-2840.
  • 19. Heiler D, McLendon G, Rogalskyj P. Synthesis and electron-transfer rates of coplanar bisporphyrins: models for (heme) protein-protein electron-transfer reactions. Journal of the American Chemical Society 1987; 109 (2): 604-606.
  • 20. Osuka A, Maruyama K, Yamazaki I, Tamai N. Synthesis of novel porphyrin dimers with twisted orientations: models for biological excitation energy and electron transfer reactions. Journal of the Chemical Society, Chemical Communications 1988; (18): 1243-1245.
  • 21. Zhao H, Liao J, Ning J, Xie Y, Cao Y et al. Efficient synthesis of novel bis (dipyrromethanes) with versatile linkers via indium (III) chloride‐ catalyzed condensation of pyrrole and dialdehydes. Advanced Synthesis & Catalysis 2010; 352 (17): 3083-3088.
  • 22. Guo C, Sun S, He Q, Lynch VM, Sessler JL. Pyrene-linked formylated bis (dipyrromethane): a fluorescent probe for dihydrogen phosphate. Organic letters 2018; 20 (17): 5414-5417.
  • 23. Tong QX, Lai SL, Chan MY, Zhou YC, Kwong HL et al. A high performance nondoped blue organic light-emitting device based on a diphenylfluoranthene-substituted fluorene derivative. The Journal of Physical Chemistry C 2009; 113 (15): 6227-6230.
  • 24. Liu F, Xie LH, Tang C, Liang J, Chen Q.-Q et al. Facile synthesis of spirocyclic aromatic hydrocarbon derivatives based on o-halobiaryl route and domino reaction for deep-blue organic semiconductors. Organic Letters 2009; 11 (17): 3850-3853.
  • 25. Liu WJ, Zhou Y, Zhou QF, Ma Y, Pei J. Shape-persistent elliptic macrocycles composed of polycyclic aromatic hydrocarbons: Synthesis and photophysical properties. Organic Letters 2008; 10 (11): 2123-2126.
  • 26. Wu J, Pisula W, Müllen K. Graphenes as potential material for electronics. Chemical Reviews 2007; 107 (3): 718-747.
  • 27. Yan Q, Zhou Y, Ni BB, Ma Y, Wang J et al. Organic semiconducting materials from sulfur-hetero benzo [k] fluoranthene derivatives: Synthesis, photophysical properties, and thin film transistor fabrication. The Journal of Organic Chemistry 2008; 73 (14): 5328-5339.
  • 28. Chiechi RC, Tseng RJ, Marchioni F, Yang Y, Wudl F. Efficient blue‐light‐emitting electroluminescent devices with a robust fluorophore: 7, 8, 10‐triphenylfluoranthene. Advanced Materials 2006; 18 (3): 325-328.
  • 29. Suzuki K, Seno A, Tanabe H, Ueno K. New host materials for blue emitters. Synthetic Metals 2004; 143 (1): 89-96.
  • 30. Tseng RJ, Chiechi RC, Wudl F, Yang Y. Highly efficient 7, 8, 10-triphenylfluoranthene-doped blue organic light-emitting diodes for display application. Applied Physics Letters 2006; 88 (9): 093512.
  • 31. Bhandari S, Ray S. A novel synthesis of bisbenzyl ketones by DCC induced condensation of phenylacetic acid. Synthetic Communications 1998; 28 (5): 765-771.
  • 32. Keshtov M, Mal’tsev E, Pozin S, Marochkin D, Perevalov V et al. In synthesis and photo-and electrophysical properties of conjugated copolyfluorenes with 7, 8, 10-triarylfluoranthene fragments in the main chain. Doklady Chemistry 2012; 0: 23-29.
  • 33. Farquhar AK, Fitchett CM, Dykstra HM, Waterland MR, Brooksby PA et al. Diels–Alder reaction of anthranilic acids: a versatile route to dense monolayers on flat edge and basal plane graphitic carbon substrates. ACS Applied Materials & Interfaces 2016; 8 (35): 23389-23395.
  • 34. Mata JA, Falomir E, Llusar R, Peris E. Preparation, properties and coordination of new conjugated ferrocenyl-based ligands with an endcapped nitrile. Journal of Organometallic Chemistry 2000; 616 (1-2): 80-88.
  • 35. Pye C, Fronczek FR, Isovitsch R. The synthesis, photophysical characterization, and X‐ray structure analysis of two polymorphs of 4, 4′‐Diacetylstilbene. Helvetica Chimica Acta 2010; 93 (6): 1162-1171.
  • 36. Paolesse R, Pandey RK, Forsyth TP, Jaquinod L, Gerzevske KR et al. Stepwise syntheses of bisporphyrins, bischlorins, and biscorroles, and of porphyrin− chlorin and porphyrin− corrole heterodimers. Journal of the American Chemical Society 1996; 118 (16): 3869-3882.
  • 37. Mongin O, Porres L, Moreaux L, Mertz J, Blanchard-Desce M. Synthesis and photophysical properties of new conjugated fluorophores designed for two-photon-excited fluorescence. Organic Letters 2002;4 (5): 719-722.
  • 38. Pavia D, Lampman G, Kriz G, Vyvyan J. Introduction to Spectroscopy. Boston, MA, USA: Cengage Learning; 2008.
  • 39. Madhu S, Ravikanth M. Synthesis, spectral, electrochemical, and anion binding properties of 3, 5-bis (dipyrromethanyl) borondipyrromethenes. Inorganic chemistry 2012; 51 (7): 4285-4292.
  • 40. Saranya G, Kolandaivel P, Senthilkumar K. Optical absorption and emission properties of fluoranthene, benzo [k] fluoranthene, and their derivatives. A DFT study. The Journal of Physical Chemistry A 2011; 115 (51): 14647-14656.
  • 41. Han L, Ye K, Li C, Zhang Y, Zhang H et al. Thermally stable and highly luminescent green emissive fluorophores with acenaphtho [1, 2‐k] fluoranthene cores and aromatic amine groups. Chem Plus Chem 2017;82 (2): 315-322.