AbstractsChemistry

Use of cyclodextrin to impose rotational restriction of luminogens with aggregation-induced emission property

by Po-Chiao Huang




Institution: NSYSU
Department:
Year: 2015
Keywords: Cyclodextrin; Jeffamine; Polystyrene; rotational restriction; Aggregation-induced emission
Posted: 02/05/2017
Record ID: 2093724
Full text PDF: http://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0629115-114946


Abstract

In Chapter 1, Because restricted molecular rotation is the main mechanism responsible for the aggregation-induced emission (AIE), a Jeffamine-included polyrotaxane (JCD) was therefore used in this study as rigid template to impose effective rotational restriction on the AIE-active luminogen of 1,2-bis(2,4-dihydroxybenzylidene)hydrazine (CN4OH). Besides rigidifying the flexible Jeffamine chain, the β-cyclodextrin (β-CD) rings of JCD also provided hydroxyl (OH) groups to hydrogen bond to the OHs of CN4OH, furnishing emissive CN4OH/JCD(x/y) (x/y: molar ratio between CN4OH and JCD) blends with emission efficiency higher than the pure CN4OH itself. Dependent on the composition of the blends, CN4OHs in the blends are arrayed differently to experience varied levels of rotational restriction and thus emit with an intensity correlated with molecular arrangement of the CN4OHs in the blends. The relationship between molecular arrangement, restricted molecular rotation and AIE-oriented emission behavior is the focus of this study. In Chapter 2, 3,4-diphenyl-2,5-bis(4-styryl)thiophene(TP2S)with AEE property showed 2,5-diphenylethene arms emission and tetraphenylthiophene (TP) center emission. β-CD were used as host molecule to encapsulate TP2S and showed an enhanced center emission and a decreased arm emission. Due to the rotational restriction, the TP2S/CD(x/y) (x/y: molar ratio between TP2S and β-CD)complex with emission intensity higher than the pure TP2S. In order to hinder TP2S slip out from β-CD, polymeric PS was used as template to grip the encapsulated TP2Ss through the Ï-Ï interactions of the aromatic phenyl rings in TP2S and in PS.When bind to PS, TP2S/CD/PS blends with higher emission intensity than the TP2S/CD complex. Advisors/Committee Members: You-wang Jiang (chair), Shiao-Wei Kuo (chair), Li-Jhen Her (chair), Lie-Li Ling (chair), Jin-Long Hong (committee member).