Acridine-Coumarin hybrid compounds: having fluorescent properties both in solid state and in solution


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Demirkol O., Vayısoğlu Giray E. S.

Anatolian Conference 5th on Organic Chemistry, Antalya, Türkiye, 3 - 05 Şubat 2025, ss.78, (Özet Bildiri)

  • Yayın Türü: Bildiri / Özet Bildiri
  • Basıldığı Şehir: Antalya
  • Basıldığı Ülke: Türkiye
  • Sayfa Sayıları: ss.78
  • Çukurova Üniversitesi Adresli: Evet

Özet


Fluorescent organic molecules have continued attractive for the attention of scientists for more than a century due to their favourable properties, such as excellent sensitivity, good specificity, fluorescent probes for disease-associated bioactive molecule imaging a large linear range of analysis and ease of handling [1-3]. Conventional organic fluorescent molecules usually suffering from the aggregation- caused quenching problem. They usually have small Stokes shifts and poor photostability. Hence, their practical application is greatly restricted. As a first time, at 2001, silole derivatives was reported as aggregation-induced emission (AIE) molecules [4]. AIE luminogens have twisted structures which can restrict intramolecular motion, and resulting in enhanced fluorescence intensity in aggregates. In this study, two new Acridine-Coumarin derivatives (Ac-COU1 and Ac-COU2) which have large Stokes shifts and quantum yields in both solution and solid states were synthesed via three relatively simple steps (Figure 1). Ac-COU1 solid powder shows a bright yellow emission with a quantum yield of 22% and Stokes shift 194 nm. In buffer solution, Stokes shift was observed as 157.9 nm and quantum yield was 29% (Table 1 and Figure1). Ac-COU2 solid powder shows a bright blue emission with a quantum yield of 31% and Stokes shift 174.01 nm. In buffer solution, Ac-COU2 showed a Stokes shift 157.9 nm and quantum yield of 45% (Table 1 and Figure2).

Figure1. New fluorescence active acridine-coumarin derivatives in both solution and solid states

Table 1. Characteristics of Ac-COU2 and Ac-COU2 in the solid-state and buffer solution

 

Entry

λEm (nm)

λEx (nm)

Stokes Shift (nm)

F

Ac-COU1 (in buffer)

411.96

254.06

157.90

0.29

Ac-COU1 solid state

424.00

230.00

194.00

0.22

Ac-COU2 (in buffer)

413.93

262.00

151.93

0.45

Ac-COU1 solid state

436.06

262.00

174.06

0.31

 

A

 

 

 

B

 

 

Figure 2. Photographs of Ac-COU1and Ac-COU 2 under daylight and UV light