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TDDFT investigation of fluorescence properties of luciferin and oxyluciferin analogs bearing an amino group

Paper ID Volume ID Publish Year Pages File Format Full-Text
28046 44057 2012 10 PDF Available
Title
TDDFT investigation of fluorescence properties of luciferin and oxyluciferin analogs bearing an amino group
Abstract

Chemical origin of high chemiluminescence efficiency of firefly luciferin remains an intriguing subject. Developing more efficient fluorescent marked compounds based on the firefly luciferin is in full swing for application in gene expression and gene regulation, and imaging of live tissues fields. Thus, a series of luciferin analogs bearing an amino group of aminoluciferin (AL), quinolylaminoluciferin (QAL), naphthylaminoluciferin (NAL), coumarylaminoluciferin (CAL) and anthrylaminoluciferin (AAL), pyrenylaminoluciferin (PAL) and corresponding keto form oxides were studied in this work, and the ground and excited state properties of them have been calculated by using time dependent density functional (TDDFT) methods in the gas phase, dimethylsulfoxide (DMSO) solution and hydrophobic environment. The results suggested that replacing aminobenzothiazole moiety of firefly luciferin with the larger rigid moieties, the absorption spectra shift to the blue. Bio-heterojunction concept was employed to explain the higher degree of spatial overlap of corresponding orbitals for CAOL, AAOL and PAOL, an important factor to be of beneficial to enhance fluorescence efficiency. In order to further explain the high fluorescence efficiency of CAOL, the process of nonradiative decay is also investigated. Comparing the energy difference of the corresponding singlet and triplet excited states in intersystem crossing and internal conversion, the reasons is qualitatively explained for the high fluorescence efficiency of CAOL. The investigation result for their emission spectra suggested that the emission maximum of AAOL is similar to firefly in nature. The influence of substituent on fluorescent emission was discussed.

► High rigidity and torsion angle obviously influence the absorption and emission spectra. ► Replacing aminobenzothiazole moiety with the larger rigid moieties, the absorption spectra shift to the blue. ► Using bio-heterojunction concept analyzed the degree of spatial overlap of transition orbitals. ► The higher overlapping volume of the transition orbitals will enhance their fluorescence efficiency.

Keywords
Luciferin analog; Oxyluciferin analog; Bio-heterojunction analysis; TDDFT calculation
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TDDFT investigation of fluorescence properties of luciferin and oxyluciferin analogs bearing an amino group
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 243, 1 September 2012, Pages 7–16
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us