Modulation of internal charge transfer (ICT) in a bay region hydroxylated perylenediimide (PDI) chromophore: a chromogenic chemosensor for pH

Date

2005-08-29

Author

Yukruk, F
Akkaya, EU

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

50
views

0
downloads

A novel perylenediimide derivative which has a bay region hydroxyl function behaves as a pH-sensitive dye. The deprotonation of the aryl-OH yields a green solution with a lambda(max) x of 692 nm and this deprotonated form has strong internal charge transfer characteristics. On reprotonation in acidic solutions, the typical PDI absorbance spectrum is restored. The experimentally determined pK(a) (7.45) is very close to physiological pH, therefore the most significant changes in color take place in the vicinity of this pH value.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/65566

Journal

TETRAHEDRON LETTERS

DOI

https://doi.org/10.1016/j.tetlet.2005.06.122

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis and properties of a novel redox driven chemiluminescent material built on a terthienyl system Atilgan, Nurdan; Algi, Fatih; Önal, Ahmet Muhtar; CİHANER, ATİLLA (Elsevier BV, 2009-07-18) A novel redox driven chemiluminescent material built on a terthienyl system, namely 5,7-di-ethylenedioxythiophen-2-yl-2,3-dihydro-thieno[3,4-d]pyridazine-1,4-dione (ETE-Lum), which is soluble in both organic media and basic aqueous solution was synthesized and characterized. Furthermore, its polymer, PETE-Lum, which is one of the most rare examples of chemiluminescent polymeric materials bearing a pyridazine unit, was obtained successfully by electrochemical means. Both of the materials give chemiluminescen...
Intermolecular heterocyclization of alkynones with 2-mercaptoacetaldehyde under metal-free conditions: synthesis of 2,3-disubstituted thiophenes Vatansever, Erol Can; Kilic, Kubra; Ozer, Merve Sinem; KOZA, GANİ; Menges, Nurettin; Balcı, Metin (Elsevier BV, 2015-09-30) A concise and regioselective approach for the synthesis of 2,3-disubstituted thiophene derivatives has been developed. The synthetic strategy relies on the reaction of an in situ generated 2-mercaptoacetaldehyde with various alkynones. Furthermore, we calculated the energy gap between the HOMO and the LUMO orbitals of all compounds and observed that the introduction of a strong electron-withdrawing group decreased the HOMO-LUMO energy gap.
Divergent synthesis of polysubstituted isoxazoles, isoxazoline N-oxides, and dihydroisoxazoles by a one-pot cascade reaction Rouf, Abdul; ŞAHİN, Ertan; Tanyeli, Cihangir (Elsevier BV, 2017-01-26) An efficient one-pot synthesis of a new class of 3,4,5-trisubstituted isoxazoline N-oxides/isoxazoles and dihydroisoxazoles is developed by a green approach from aromatic and aliphatic aldehydes by controlling the reaction conditions. Aldehydes were reacted with ethyl nitroacetate in the presence of DABCO as a catalyst under ultrasonication. In aromatic aldehydes, isoxazoline N-oxides were obtained exclusively when the reaction was carried out at 40 degrees C, but raising the temperature to 80 degrees C iso...
Reinvestigation of the synthetic and mechanistic aspects of Mn(III) acetate mediated oxidation of enones Demir, Ayhan Sıtkı; Reis, O; Igdir, AC (Elsevier BV, 2004-04-05) Mn(OAc)(3) mediated alpha'-acetoxylation of alpha,beta-unsaturated enones is reinvestigated from a synthetic and mechanistic point of view and an improved procedure based on the use of acetic acid as a co-solvent is presented. Excellent results were obtained for a variety of structurally diverse and synthetically important enones under the optimized conditions.
High temperature bromination. Part 12: Bromination of 7-oxabenzonorbornadiene: Synthesis of 2,3-dibromo-7-oxabenzonorbornadiene Altundas, A; Dastan, A; McKee, MM; Balcı, Metin (Elsevier BV, 2000-08-11) The electrophilic addition of bromine to 7-oxabenzonorbornadiene (8) at 0 degrees C led in high yield to the formation of dibromoaldehyde 10. However, high-temperature bromination of 8 in carbontetrachloride at 77 degrees C gave non-rearranged products 17 and 18. From the elimination of non-rearranged products, 2-bromo-7-oxabenzonorbornadiene (12) was obtained. Similarly, bromination of monobromide 12 at 77 degrees C yielded the non-rearranged tribromides 19 and 20 while bromination of 12 at 0 degrees C gav...

Citation Formats

F. Yukruk and E. Akkaya, “Modulation of internal charge transfer (ICT) in a bay region hydroxylated perylenediimide (PDI) chromophore: a chromogenic chemosensor for pH,” TETRAHEDRON LETTERS, pp. 5931–5933, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/65566.