Sains Malaysiana 47(5)(2018): 903–908

http://dx.doi.org/10.17576/jsm-2018-4705-05

 

Isolation and Photophysical Properties of Di- and Tri-substituted Natural Anthraquinones from Malaysian Morinda citrifolia

(Pengasingan dan Sifat Fotofizikal Antraquinon Semula Jadi Tertukarganti-Di dan Tri daripada Morinda citrifoliadi Malaysia)

 

NABILA ELYANA ADNAN, NUR ATIQAH MOHD NASUHA, ZANARIAH ABDULLAH, YEUN-MUN CHOO* & HAIRUL ANUAR TAJUDDIN

 

Chemistry Department, University of Malaya, Jalan Universiti, 50603 Wilayah Persekutuan, Kuala Lumpur, Malaysia

 

Received: 21 August 2017/Accepted: 5 December 2017

 

 

ABSTRACT

Five di- and tri-substituted natural anthraquinones, i.e. nordamnacanthal (1), damnacanthal (2), rubiadin (3), 1-methoxy-2-methyl-3-hydroxyanthraquinone (4) and 1-hydroxy-3-methoxyanthraquinone (5) were subjected to photophysical studies. The results indicated that steric hindrance and intramolecular hydrogen bonding are important factors that affect absorption and emission spectral of these natural anthraquinones. Besides that, emission properties were significantly enhanced with formation of intramolecular hydrogen bonding in 1,3-dihydroxy-2-aldehyde tri-substituted anthraquinone 1. This gave rise to formation of two additional quasi aromatic rings extending the π-conjugation system in the anthraquinone structure.

 

Keywords: Absorption spectral; anthraquinone; emission spectral; intramolecular hydrogen bonding; photophysical properties

 

ABSTRAK

Lima antraquinon semula jadi, iaitu nordamnacanthal (1), damnacanthal (2), rubiadin (3), 1-metoksi-2-metil-3-hidroksiantraquinon (4) dan 1-hidroksi-3-metoksiantraquinon (5) digunakan dalam kajian sifat fotofizikal. Keputusan kajian menunjukkan bahawa penghalang sterik dan ikatan hidrogen intramolekul adalah faktor penting yang mempengaruhi spektrum penyerapan dan pelepasan antraquinon semula jadi. Selain itu, sifat fotofizikal pemancaran antraquinon 1 tertukarganti-tri 1,3-dihidroksi-2-aldehid dipertingkatkan dengan pembentukan ikatan hidrogen intramolekul. Pembentukan ikatan hidrogen intramolekul ini membolehkan pembentukan dua gelang aromatik kuasi tambahan dan memanjangkan sistem konjugasi-π dalam struktur antraquinon.

 

Kata kunci: Antraquinon; ikatan hidrogen intramolekul; sifat fotofizikal; spektra pelepasan spektra penyerapan

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*Corresponding author; email: ymchoo@um.edu.my