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Red Emissive BODIPY Dyes As Sensitizers for Near-Infrared Emission of Lanthanide Complexes & Structural & Spectroscopic

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Red Emissive BODIPY Dyes As Sensitizers for Near-Infrared Emission of Lanthanide Complexes & Structural & Spectroscopic Eastern Illinois University The Keep Masters Theses Student Theses & Publications 2017 Red Emissive BODIPY Dyes as Sensitizers for Near-Infrared Emission of Lanthanide Complexes & Structural & Spectroscopic Studies of Quinoline-Functionalized BODIPY Dyes Adedayo Ayodeji Kukoyi Eastern Illinois University This research is a product of the graduate program in Chemistry at Eastern Illinois University. Find out more about the program. Recommended Citation Kukoyi, Adedayo Ayodeji, "Red Emissive BODIPY Dyes as Sensitizers for Near-Infrared Emission of Lanthanide Complexes & Structural & Spectroscopic Studies of Quinoline-Functionalized BODIPY Dyes" (2017). Masters Theses. 2910. https://thekeep.eiu.edu/theses/2910 This is brought to you for free and open access by the Student Theses & Publications at The Keep. It has been accepted for inclusion in Masters Theses by an authorized administrator of The Keep. For more information, please contact [email protected]. TheGraduate School EASTERNILLINOIS UNIVERSITY­ Thesis Maintenance and Reproduction� Certificate FOR: Graduate Candidates Completing Theses in Partial Fulfillment of the Degree Graduate Faculty Advisors Directing the Theses RE: Preservation, Reproduction, and Distribution of Thesis Research Preserving, reproducing, and distributing thesis research is an important part of Booth Library's responsibility to provide access to scholarship. In order to further this goal, Booth Library makes all graduate theses completed as part of a degree program at Eastern Illinois University available for personal study, research, and other not-for-profit educational purposes. Under U.S.C. § the library may 17 108, reproduce and distribute a copy without infringing on copyright; however, professional courtesy dictates that permission be requested from the author before doing so. Your signatures affirm the following: • The graduate candidate is the author of this thesis. • The graduate candidate retains the copyright and intellectual property rights associated with the original research, creative activity, and intellectual or artistic content of the thesis. The graduate candidate certifies her/his compliance with federal copyright law (Title of the U. • 17 S. 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Red Emissive BODIPY Dyes as Sensitizers for Near-Infrared Emission of Lanthanide Complexes & Structural Spectroscopic Studies of Quinoline-Functionalized BODIPY Dyes & (TITLE) BY Adedayo Ayodeji Kukoyi THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF Masters of Science in Chemistry IN THE GRADUATE SCHOOL, EASTERN ILLINOIS UNIVERSITY CHARLESTON, ILLINOIS 2017 YEAR I HEREBY RECOMMEND THAT THIS THESIS BE ACCEPTED AS FULFILLING THIS PART OF THE GRADUATE DEGREE CITED ABOVE 8 l1r//.J- THESIS COMMITTEE CHAIR DATE DEPARTMENT/SCHOOL CHAIR DATE OR CHAIR'S DESIGNEE tJ8/1S-/.2.>17 THESIS CeMMITTEE MEMB�R �)DATE i"HE�COMMITTEE MEMBER DATE THESIS �MMITTEE MEMBER DATE THESIS COMMITTEE MEMBER � DATE Red Emissive BODI PY Dyes as Sensitizers for Near-Infrared Emission of Lanthanide Complexes & Structural & Spectroscopic Studies of Quinoline-Functionalized BODI PY Dyes Adedayo Ayodeji Kukoyi Research Advisor: Dr. Hongshan He Eastern Illinois University Chemistry Department ii Table of Contents Table of Contents .................................................................................................................. ..... .............. iii Abbreviations. ..........................................................................................................................................viii Abstract ...................................................................................................................................................... ix Acknowledgements ..................................................... ........ ............... ................................... .................. xi List of Figures... ........................................................................ ................................. ............... ......... ....... xii List of Tables.................................................. .... ........................ ........................................ ........... .......... xvi 1.0 INTRODUCTION ................................................................................................................................. 1 1.1 Overview................................... ........................................................................................................... 1 1.2 General Properties of Lanthanide ions ........................... ....................... ........................................ 2 1.3 Lanthanide in Biological Analysis.. ................................................................................................... 3 1.4 Lanthanide ion Sensitization by Chromophores.................. .......................................................... 4 1.5 Dexter and Forster Energy Transfer Mechanism ........................................................................... 6 1.6 Overview of lanthanide Complexes........... ........................ ... .............. ............................................ 8 1.6.1 Porphyrin Complexes ........................................................................................................... 9 1.6.2 Pyridine ............ ... ............... ......... .. ....... .. ....... ..... ... ........... .. ............... ... .. ....... 11 Complexes 1.6.3 Complexes of bipyridine............................. ............ .......... ...... .......................................... 11 1.6.3.1 Terpyridine derivatives ............... .................................................................... 15 1.6.3.2 Hydroxyquinoline Complexes........... .... .............. ........................................... 17 1. 7 Background on BODI PY dyes ......... ..... ..... .......................................................... ............. ... ......... 18 1.7.l Feature of BODIPY dyes.......................... .... ..... ......... ..... .................................................... 18 1.7.2 Fundamental Properties of BODIPY dyes ............................................................ ............. 19 iii 1.7.3 Modification of BODIPY dyes for enhanced photophysical properties......................... 20 1.7.4 BODIPY dyes fluorescence quenching mechanism via photo-induced electron transfer............................. ...................................................................................................... 23 1.7.5 BODIPY dyes as triplet photosensitizers and its application in NIR luminescence probes.................................................................................................................................... 27 1.7.5.1 BODIPY dyes as triplet photosensitizers....... ...............................................27 1.7.5.2 BODIPY dyes Application in designing NIR luminescent probes .............. 28 1.8 Motivation ..........................................................................................................................................31 1.9 Objectives ........................................................................................................................................... 32 2.0 EXPERIMENTAL. ........... ...... .................. ........... ............. ... ... ............................................................ ... 33 2.1 General ...................................................................................................................................... ..........33 2.1.1 Materials ........................................................................................................................... 33 2.1.2 lnstruments ........................................................................................................................34 2.2 Synthesis....................... ..................................................................................................................... 35 2.2.1 Synthesis of AHl...............................
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