How to say his coolness has alienated his friends. in Japanese

1)彼の彼の(kano) (adj-pn) that冷たno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbさがさが(saga) (adj-t,adv-to) precipitous彼の彼の(kano) (adj-pn) that友人友人(yuujin) (n) friendを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,疎遠疎遠(soen) (adj-na,n,adj-no) estrangement/neglect/silenceに(ni) (prt) indicates such things as location of person or thing, location of short-term action, etc.させてしまったno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb。(。) Japanese period "."    
kano tsumeta saga kano yuujin wo soen nisaseteshimatta 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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